Home Journals Articles Updates About
CN
image
收藏切换
Alkylarylation of alkenes with arylsulfonylacetate as bifunctional reagent via photoredox radical addition/Smiles rearrangement cascade
收藏切换
PDF
Chonglong Hea, Yulong Wanga, Quan-Xin Lib, Zichen Yana, Keyuan Zhanga, Shao-Fei Nib, Xin-Hua Duana, Le Liu*, a
Chinese Chemical Letters | 2025, 36(5) : 110253
Less
收藏切换
Chinese Chemical Letters | 2025, 36(5): 110253
• Communication •
Alkylarylation of alkenes with arylsulfonylacetate as bifunctional reagent via photoredox radical addition/Smiles rearrangement cascade
Full
Chonglong Hea, Yulong Wanga, Quan-Xin Lib, Zichen Yana, Keyuan Zhanga, Shao-Fei Nib, Xin-Hua Duana, Le Liu*, a
Affiliations
  • a School of Chemistry, Engineering Research Center of Energy Storage Materials and Devices, Ministry of Education, Xi’an Key Laboratory of Sustainable Energy Material Chemistry, Xi’an Jiaotong University, Xi’an 710049, China
  • b Department of Chemistry, Key Laboratory for Preparation and Application of Ordered Structural Materials of Guangdong Province, Shantou University, Shantou 515063, China
Published: 2025-05-15 doi: 10.1016/j.cclet.2024.110253
Outline
收藏切换

The radical difunctionalization of alkenes with sulfonyl bifunctional represents a powerful and straightforward approach to access functionalized alkane derivatives. However, both the mechanistic activation mode and the substrate scopes of this type of radical difunctionalizations are still limited. We demonstrate herein a modular photoredox strategy for the difunctionalization of alkenes, employing arylsulfonyl acetate as the bifunctional reagent. This approach involves a radical addition/Smiles rearrangement cascade process, offering a robust alternative for the synthesis of valuable γ,γ-diaryl and γ-aryl esters. A complementary oxidative bifunctional reagents activation mode is identified to govern the radical cascade reactions, facilitating the simultaneous incorporation of aryl and carboxylate-bearing alkyl groups into the alkenes with excellent diastereoselectivity. Noteworthy features of this method include mild reaction conditions, organophotocatalysis, high atom- and step-economy, excellent functional group compatibility and great structural diversity.

Radical difunctionalization  /  Bifunctional reagents  /  Smiles rearrangement  /  Photoredox  /  γ,γ-Diaryl and γ-aryl ester
Chonglong He, Yulong Wang, Quan-Xin Li, Zichen Yan, Keyuan Zhang, Shao-Fei Ni, Xin-Hua Duan, Le Liu. Alkylarylation of alkenes with arylsulfonylacetate as bifunctional reagent via photoredox radical addition/Smiles rearrangement cascade[J]. Chinese Chemical Letters, 2025 , 36 (5) : 110253 - . DOI: 10.1016/j.cclet.2024.110253
Full Text
Less
Difunctionalization of alkenes provides a robust tool for converting simple alkenes into complex molecules, which is of high interest and challenging from both academic and industrial perspectives [1-7]. The simultaneous formation of multiple bonds using just one bifunctional reagent has become state-of-the-art in achieving this target [8-17]. Numerous examples of bifunctional reagents-mediated difunctionalization of alkenes have been disclosed in recent decades due to the rapid development of electrocatalysis [18-20] and photocatalysis [18,21-30]. Among them, the sulfonyl bifunctional reagent stands out for enabling alkene difunctionalization via a radical-induced functional group migration process, proving to be one of the most efficient approaches [31-34]. In general, those reactions could be categorized mechanistically into the following two types: (1) Single-electron oxidation of the electron-rich alkenes to generate the key active radical cation species. Then, bifunctional reagents nucleophilic attach the radical cation and engage in the following intramolecular Smiles rearrangement to achieve the difunctionalization (Fig. 1A) [35-37]. (2) Instead of alkene oxidation, single-electron reduction of sulfonyl alkyl bromide bifunctional reagents yields the electrophilic radical species, which subsequently undergo radical addition to styrenes. Then, the benzyl radical goes through ipso attack, leading to 1,4-functional group migration to deliver the difunctionalized products (Fig. 1B) [32,33,38-46]. Pioneered by Stephenson and Zhu, various efficient desulfonylative difunctionalizations of alkenes with these activation modes have been reported for incorporating amino or alkyl units and (hetero)aryl units across alkenes. In addition, an asymmetric radical difunctionalization was also realized by the Nevado group, employing chiral sulfinamide as the auxiliary [47,48]. Nevertheless, both the mechanistic activation mode and the substrate scopes in alkene radical difunctionalizations are still limited. More easily accessible and functional group-compatible bifunctional reagents, as well as complementary mechanistic activation modes, are still highly desirable.
Recently, arylsulfonylacetate has been independently developed as a bifunctional reagent for the difunctionalization of unsaturated carbon-carbon bonds by both our research group [49,50] and others [51]. As an extension of our ongoing exploration into radical chemistry [52-57], we conceived a strategy employing arylsulfonylacetate as a bifunctional reagent for the difunctionalization of styrenes to access γ,γ-diaryl and γ-aryl ester compounds, which are frequently encountered in bioactive compounds and natural products (Fig. 1D) [58-60]. Subsequently, a crucial mechanistic question arose, specifically concerning the activation mode that would govern the anticipated transformation (Fig. 1C). This consideration holds significant implications for both the substrate scope and the overall efficiency of the proposed method. Theoretically, the acidic proton (pKa 13–16) in the active methylene site would be readily deprotonated under basic conditions to give a nucleophilic enolate, which would trap alkene radical cation via alkene activation mode. Conversely, the bond dissociation energy of the C‒H bond at the active methylene site falls within the range of approximately 96 kcal/mol, rendering selective hydrogen atom abstraction (HAA) thermodynamically feasible [50]. Then, the generation of a highly electrophilic radical species, facilitated through either a suitable hydrogen atom abstraction (HAA) or a single electron oxidation process appears operational to initiate the difunctionalization via bifunctional reagent activation mode.
To test the feasibility of our hypothesis and inspire the future development of novel bifunctional reagents for alkene difunctionalization, we selected arylsulfonyl acetate 1aa and trans-anethole 2aa as model substrates for our initial investigations. To our delight, when 4CzIPN was employed as the photocatalyst and K3PO4 as the base, the desired γ,γ-diaryl ester 3aa could be formed in 76% yield with excellent diastereoselectivity (Fig. 2A). Then, cyclic voltammetry (CV) measurements were carried out to elucidate the oxidative process underlying this photocatalytic event. Compound 1aa displayed the first distinct oxidation at Ep/2 = + 0.68 V (vs. SCE in CH3CN) in the presence of base, while that of trans-anethole 2aa was determined to be Ep/2 = + 1.30 V (vs. SCE in CH3CN) which is consistent with the reported data (Fig. 2B) [61,62]. Given the redox potential of the photocatalyst 4CzIPN (*E1/2 (PC*/PC- = +1.35 V vs. SCE in MeCN) enables the thermodynamically favorable oxidation of both reactants, further experiments were performed. Stern-Volmer fluorescence quenching experiments revealed a notably faster quenching rate for 1aa in the presence of a base compared to 2aa, while pure 1aa is entirely unresponsive (Fig. 2C). Moreover, upon the introduction of 2.0 equiv. of the radical scavenger TEMPO into the reaction mixture, the reaction was entirely inhibited, concomitant with the detection of TEMPO adduct 5 (Fig. 2D). These results demonstrate that the crucial radical species derived from bifunctional reagent 1aa actively participated in this cascade transformation. As anticipated, Ir(ppy)3 possessing a relatively low oxidative potential (EIr(Ⅱ)/Ir(Ⅲ)* = +0.31 V) [63,64] exhibited completely inertness in the reaction. While Ru(bpy)3Cl2 with an oxidation potential positioned between those of 1aa and 2aa was employed as the photocatalyst, the desired product 3aa can be obtained with a 72% yield. Intriguingly, switching the photocatalyst to Mes-Acr+-MeClO4- or TPT which were commonly used for alkene radical cation species generation [65-70], resulted in no detection of 3aa (Fig. 2E). Taken together, these data provide support for single-electron oxidation of bifunctional reagent 1aa to initiate this radical difunctionalization reaction.
Further optimization of reaction parameters, including the photocatalyst, base, and solvent, led us to identify the optimal conditions to achieve an 84% yield of product 3aa with >20:1 diastereoselectivity (For details, see Supporting information). Control experiments indicated that the photocatalyst, light irradiation, and K3PO4·3H2O were all ciritical to the cascade transformation, as the absence of any of these components resulted in no detection of the desired product (Fig. 2F). To the best of our knowledge, this reaction not only presents a novel alternative for the consecutive formation of multiple C‒C bonds, leading to the synthesis of γ,γ-diaryl esters but also introduces a complementary mechanistic activation mode for the sulfonyl bifunctional reagent-mediated difunctionalization of alkenes.
With the optimal conditions in hand, our initial focus was on exploring the structural diversity concerning the migrating aromatic ring in arylsulfonylacetate bifunctional reagents (Scheme 1). Phenyl rings containing various substituents, including electron-donating groups such as methyl, tert–butyl, and methoxy, as well as electron-withdrawing groups (halogens), were all found to be compatible to provide the corresponding γ,γ-diarylesters (3aa-3ap) in 20% to 84% yields with excellent diastereoselectivity. It is worth noting that the structure of 3aa was ambiguously confirmed by X-ray analysis of the corresponding acid derivative (CCDC: 2323478). Generally, bifunctional reagents featuring electron-withdrawing groups on the phenyl rings exhibited more efficient reactions with alkenes, resulting in higher yields of the corresponding γ,γ-diarylesters compared to those with electron-donating groups. This phenomenon was attributed to the favorable π-π stacking interaction between the electron-deficient aryl ring of the bifunctional reagent and the electron-rich PMP rings [71]. This interaction is believed to contribute to lowering the energy barrier for the aryl migration process [36]. Significantly, functional groups like halides, amenable to subsequent derivatization, were well-tolerated, yielding the corresponding products in good yields. Furthermore, heteroaryl groups such as pyridine and thiophene were found to be compatible under the standard conditions, yielding γ,γ-diarylesters 3ao and 3ap in moderate yields.
We extended our investigation to explore the diversity of substituents in the electron-rich internal alkenes (Scheme 2). Both mono- and multi-substituted alkoxy phenyl rings in olefins resulted in the production of the target products with high yields (3ba-3bd). Notably, various protecting groups for the phenol moiety, including benzoyl, Boc, and triflate, were all compatible under the standard conditions (3bd-3bg). Particularly, the free hydroxyl group remained intact, yielding the corresponding difunctionalized product 3bh in a moderate yield of 65%. Furthermore, alkyl chains containing halide and cyano functionalities were also well-tolerated under the standard conditions, affording the products 3bj-3bl. It is noteworthy that an electron-rich styrene containing a terminal alkene chain exhibits pronounced selectivity to give the expected product 3bm in moderate 65% yield. This selectivity can be attributed to the favorable π-π stacking interactions within the electron-deficient aromatic phenyl ring of 1a and the electron-rich alkene 2m. Increasing the length of the alkyl chain in the internal alkene showed negligible impact on the transformation (3bn). Trisubstituted internal alkene also proved to be effective substrate under the standard conditions, yielding the difunctionalized product 3bo bearing a quaternary center with moderate yield and diastereoselectivity. Internal alkene was also examined, but poor reactivity and diastereoselective was observed (3bp). This was attributed to the steric hindrance of the cyclic internal alkene for both the radical addition and aryl migration process. Furthermore, methylthiol and dialkylamino groups were proven to be suitable electron-donating groups under this photoredox conditions, furnishing the corresponding γ,γ-diarylesters (3bq-3bs) in moderate yields with good diastereoselectivities.
Considering the initiation of the reaction through the bifunctiomal reagent activation mode, it can be inferred that radical acceptors are not restricted solely to electron-rich anethole derivatives (Scheme 3). To validate our hypothesis, (E)–prop-1-en-1-ylbenzene, with an oxidation potential Ep/2 = +1.74 V vs. SCE in CH3CN surpassing that of the excited photocatalyst 4CzIPN (E1/2 (PC*/PC- = +1.35 V vs. SCE in MeCN), was subjected to the standard conditions. As expected, the desired difunctionalized product 3ca was formed in a moderate yield of 65%. Substituents bearing different electronic propertied were also effective precursor for the preparation of the γ,γ-diarylesters 3cb-3d In addition, heterocycle substituted internal alkene can also be tolerated under the standard conditions, affording the thiophene substituted product 3ce with a yield of 34%. The disubstituted terminal alkene exhibited relatively low reactivity to produce a quaternary-carbon-bearing γ,γ-diarylester 3cf in 20% yield. Furthermore, styrenes turned out to be completely inert under the standard conditions. Moreover, this photocatalyzed radical addition/Smiles rearrangement cascade reaction is applicable to a variety of unactivated olefins, such as terminal and internal alkenes, yielding the corresponding alkylarylated products (3ci-3cl) with moderate yields. This underscores the synthetic versatility of our approach. Notably, cyclopentene and 1,2-dihydrofuran selectively generated cis-products, which likely attributed to the formation of the most stable cis-fused intermediates from these substrates [51].
To gain additional insights in the reaction mechanism, several control experiments were performed (Scheme 4). First, standard conditions were applied to two independent experiments using trans-anethole and a 1:9 mixture of trans- and cis-anethole. In both cases, identical products were formed in comparable yields, with almost identical diastereoselectivity. This indicated that a stepwise process is involved in the reaction. In addition, a deuterium labelling experiments was performed. Introducing 5 equiv. of D2O to the reaction mixture under standard conditions resulted in the isolation of 31% yield of deuterium-labeled 3aa-D, along with the formation of 52% yield of 3aa. However, treating 3aa with D2O under the standard conditions did not lead to the detection of 3aa-D. Furthermore, when the reaction was performed in CD3CN with K3PO4 as the base, no deuterium was observed on the product. Considering the rather hydridic nature of the proton on substrate 1aa and radical polarity-match effect, we concluded that a radical polar crossover-enabled protonation might be operational in this cascade process. Moreover, we further measured the oxidation potentials of the substrates. Generally, all the arylsulfonyl acetates exhibited good compatibility with the redox potential of the photocatalyst, ranging from 0.4 V to 0.73 V, which is considerably lower than that of alkenes (1.07–1.89 V). It is worth mentioning that all the oxidation potentials for the arylsulfonyl acetates were determined in the presence of a base. This aligns with their effective fluorescence quenching observed in experiments involving a base, which indicated a deprotonation and oxidation sequence is involved. Interestingly, the dialkylamino-substituted phenyl alkene exhibited an oxidation potential of 0.56 V, even lower than that of compound 1aa. Further fluorescence quenching experiments indicated that these two alkenes are much more efficient quenchers of the photocatalyst (see Supporting information). These results suggest that different mechanisms might be operating in the cascade transformation depending on the olefinic partner (Fig. S12 in Supporting information).
Drawing upon the control experiments and prior literatures [35-37], a plausible mechanism for the majority of the difunctionalization was proposed, as depicted in Scheme 5. And it was further confirmed by density functional theory (DFT) calculations. Initially, the photocatalyst (PC) is irradiated by blue light to its excited state, which undergoes a single electron transfer event with 1a in the presence of base to afford alkyl radical Ⅰ. Electrophilic radical addition to the double bond of alkene forms benzyl radical Int1. Subsequently, radical Int1 undergoes ipso-radical addition to the aryl ring via a π-π stacked transition state TS1 with a Gibbs free energy barrier of 14.6 kcal/mol, delivering the spiroradical intermediate Int2. Fragmentation, accompanied by the extrusion of SO2 via a stepwise sequence involving TS2 and TS3, produces alkyl radical Ⅳ. The exergonicity of this transition was computed to be −20.4 kcal/mol. The transient radical Int4 is then reduced via another SET event from PC-1 followed by protonation to give the desired alkene 3, concomitantly regenerating PC to complete the photo-redox cycle. For the dialkylamino-substituted alkenes, which represent some of the electron-rich alkenes with relatively low oxidation potentials, the alkene activation mode might be involved, and a detailed discussion of the reaction mechanism is proposed in Fig. S12 (Supporting information).
In conclusion, we have unveiled a novel oxidative bifunctional reagent activation mode for the alkylarylation of alkenes under photoredox conditions using arylsulfonyl acetate as the bifunctional reagent. This metal-free radical process enables the simultaneous incorporation of carboxylate-bearing alkyl groups and (hetero)aryl rings into a wide range of olefins, thereby facilitating the synthesis of a diverse library of synthetically valuable γ,γ-diarylester derivatives. This method features mild reaction conditions, high atom- and step-economy, excellent functional group compatibility and great structural diversity. Given the current easy availability of arylsulfonylacetate bifunctional reagents, along with the ubiquity of alkenes as feedstock substrates, we anticipate this method would serve as a highly enabling platform for research endeavors aimed at synthesizing synthetic useful γ,γ-diarylester and γ-arylesters in a single operation. The success of this strategy utilizing bifunctional reagents for the difunctionalization of alkenes is expected to stimulate further investigations into this concept.
Declaration of competing interest
Less
The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.
CRediT authorship contribution statement
Less
Chonglong He: Investigation, Data curation. Yulong Wang: Methodology, Investigation. Quan-Xin Li: Software, Investigation. Zichen Yan: Methodology, Formal analysis, Data curation. Keyuan Zhang: Methodology, Data curation. Shao-Fei Ni: Writing – review & editing, Writing – original draft, Formal analysis. Xin-Hua Duan: Writing – original draft, Supervision, Project administration. Le Liu: Writing – review & editing, Writing – original draft, Supervision, Formal analysis, Conceptualization.
Acknowledgments
Less
L. Liu thanks the National Natural Science Foundation of China (No. 21901199), National Training Program of Innovation and Entrepreneurship for Undergraduates (No. S202310698011), and Xi’an Jiaotong University (No. 7121192002) for financial support. We thank Prof. Li-Na Guo and Miss Kehui Wang for vaulable discussions. We thank Dr. Lu Bai and Dr. Chao Feng at Instrument Analysis Center of Xi’an Jiaotong University for HRMS and NMR analysis.
Supplementary materials
Less
Supplementary material associated with this article can be found, in the online version, at doi:10.1016/j.cclet.2024.110253.
References
Less
1
R.N. McDonald, G. Liu, S.S. Stahl, Chem. Rev. 111 (2011) 2981–3019.
2
C. Zhang, C. Tang, N. Jiao, Chem. Soc. Rev. 41 (2012) 3464.
3
X.H. Ouyang, R. Song, M. Hu, Y. Yang, J.H. Li, Angew. Chem. Int. Ed. 55 (2016) 3187–3191.
4
X. Wang, Y.F. Han, X.H. Ouyang, R. Song, J.H. Li, Chem. Commun. 55 (2019) 14637–14640.
5
D.C. Blakemore, L. Castro, I. Churcher, et al., Nat. Chem. 10 (2018) 383–394.
6
K.R. Campos, P.J. Coleman, J.C. Alvarez, et al., Science 363 (2019) eaat0805.
7
B. Trost, Science 254 (1991) 1471–1477.
8
H.M. Huang, P. Bellotti, J. Ma, T. Dalton, F. Glorius, Nat. Rev. Chem. 5 (2021) 301–321.
9
E. Piers, Pure Appl. Chem. 60 (1988) 107–114.
10
X. Yu, Q.Y. Meng, C.G. Daniliuc, A. Studer, J. Am. Chem. Soc. 144 (2022) 7072–7079.
11
Z. Li, L. Jiao, Y. Sun, et al., Angew. Chem. Int. Ed. 59 (2020) 7266–7270.
12
A. Link, C. Fischer, C. Sparr, Angew. Chem. Int. Ed. 54 (2015) 12163–12166.
13
J.E. Erchinger, R. Hoogesteger, R. Laskar, et al., J. Am. Chem. Soc. 145 (2023) 2364–2374.
14
L.L. Liao, G.M. Cao, Y.X. Jiang, et al., J. Am. Chem. Soc. 143 (2021) 2812–2821.
15
H. Li, H. Neumann, M. Beller, X.F. Wu, Angew. Chem. Int. Ed. 53 (2014) 3183–3186.
16
J.J. Farndon, T.A. Young, J.F. Bower, J. Am. Chem. Soc. 140 (2018) 17846–17850.
17
D. Wu, N.A. Fohn, J.W. Bode, Angew. Chem. Int. Ed. 58 (2019) 11058–11062.
18
X.Y. Yu, Q.Q. Zhao, J. Chen, W.J. Xiao, J.R. Chen, Acc. Chem. Res. 53 (2020) 1066–1083.
19
Y. Yuan, A. Lei, Acc. Chem. Res. 52 (2019) 3309–3324.
20
P. Xiong, H.C. Xu, Acc. Chem. Res. 52 (2019) 3339–3350.
21
K.L. Skubi, T.R. Blum, T.P. Yoon, Chem. Rev. 116 (2016) 10035–10074.
22
J.C. Tellis, C.B. Kelly, D.N. Primer, et al., Acc. Chem. Res. 49 (2016) 1429–1439.
23
R.C. McAtee, E.J. McClain, C.R.J. Stephenson, Trends Chem. 1 (2019) 111–125.
24
W. Lee, I. Park, S. Hong, Sci. China Chem 66 (2023) 1688–1700.
25
M. Kim, Y. Koo, S. Hong, Acc. Chem. Res. 55 (2022) 3043–3056.
26
B. Lu, Z. Zhang, M. Jiang, et al., Angew. Chem. Int. Ed. 62 (2023) e202309460.
27
S. Ohmura, K. Katagiri, H. Kato, et al., J. Am. Chem. Soc. 145 (2023) 15054–15060.
28
T. Horibe, S. Ohmura, K. Ishihara, J. Am. Chem. Soc. 141 (2019) 1877–1881.
29
B.G. Cai, C. Empel, W.Z. Yao, R.M. Koenigs, J. Xuan, Angew. Chem. Int. Ed. 62 (2023) e202312031.
30
H. Fang, C. Empel, L. Atodiresei, R.M. Koenigs, ACS Catal. 13 (2023) 6445–6451.
31
Z.M. Chen, X.M. Zhang, Y.Q. Tu, Chem. Soc. Rev. 44 (2015) 5220–5245.
32
X. Wu, C. Zhu, Acc. Chem. Res. (2020) 1620–1636.
33
X. Wu, Z. Ma, T. Feng, C. Zhu, Chem. Soc. Rev. 50 (2021) 11577–11613.
34
A.R. Allen, E.A. Noten, C.R.J. Stephenson, Chem. Rev. 122 (2022) 2695–2751.
35
T.M. Monos, R.C. McAtee, C.R.J. Stephenson, Science 361 (2018) 1369–1373.
36
A.K. Allen, J. Poon, R.C. McAtee, et al., ACS Catal. 12 (2022) 8511–8526.
37
E.A. Noten, R.C. McAtee, C.R.J. Stephenson, Chem. Sci. 13 (2022) 6942–6949.
38
J. Yu, Z. Wu, C. Zhu, Angew. Chem. Int. Ed. 57 (2018) 17156–17160.
39
M. Wang, H. Zhang, J. Liu, X. Wu, C. Zhu, Angew. Chem. Int. Ed. 58 (2019) 17646–17650.
40
X. Zhang, X. Wu, Y. Chen, C. Zhu, Green Chem. 25 (2023) 4234–4238.
41
J. Yu, X. Zhang, X. Wu, et al., Chem 25 (2022) 472–482.
42
H. Zhang, M. Wang, X. Wu, C. Zhu, Angew. Chem. Int. Ed. 60 (2021) 3714–3719.
43
J. Wang, X. Wu, Z. Cao, et al., Adv. Sci. 11 (2024) 2309022.
44
Y. Wei, H. Zhang, X. Wu, C. Zhu, Angew. Chem. Int. Ed. 60 (2021) 20215–20219.
45
T. Niu, J. Liu, X. Wu, C. Zhu, Chin. J. Chem. 38 (2020) 803–806.
46
Y. Chen, X. Wu, S. Yang, C. Zhu, Angew. Chem. Int. Ed. 61 (2022) e202201027.
47
C. Hervieu, M.S. Kirillova, Y. Hu, et al., Nat. Chem. 16 (2024) 607–614.
48
C. Hervieu, M.S. Kirillova, T. Suárez, et al., Nat. Chem. 13 (2021) 327–334.
49
C. He, M. Wang, Y. Wang, et al., Sci. China Chem. 67 (2024) 2022–2028.
50
Y. Wang, S. Shen, C. He, et al., Chem. Sci. 14 (2023) 6663–6668.
51
D. Babcock, A.J. Wolfram, J.L. Barney, et al., Chem. Sci. 15 (2024) 4031–4040.
52
Y. Zhou, Q. Jiang, Y. Cheng, et al., Org. Lett. 26 (2024) 2656–2661.
53
C. He, K. Zhang, D.N. Wang, et al., Org. Lett. 24 (2022) 2767–2771.
54
K. Zhang, Y. Wang, C. He, et al., Org. Chem. Front. 9 (2022) 5599–5605.
55
C. He, M. Wang, B. Dong, et al., Green Synth. Catal. 5 (2024) 117–212.
56
Y. Zhou, L. Zhao, M. Hu, X.H. Duan, L. Liu, Org. Lett. 25 (2023) 5268–5272.
57
Y. Zheng, Y. You, Q. Shen, et al., Org. Chem. Front. 7 (2020) 2069–2074.
58
S. Kc, R.K. Dhungana, N. Khanal, R. Giri, Angew. Chem. Int. Ed. 59 (2020) 8047–8051.
59
N. Katta, Q.Q. Zhao, T. Mandal, O. Reiser, ACS Catal. 12 (2022) 14398–14407.
60
T.V.T. Nguyen, A. Bossonnet, M.D. Wodrich, J. Waser, J. Am. Chem. Soc. 145 (2023) 25411–25421.
61
M. Riener, D.A. Nicewicz, Chem. Sci. 4 (2013) 2625.
62
D. Nicewicz, H. Roth, N. Romero, Synlett 27 (2016) 714–723.
63
Y. Sakakibara, K. Murakami, ACS Catal. 12 (2022) 1857–1878.
64
K. Kwon, R.T. Simons, M. Nandakumar, J.L. Roizen, Chem. Rev. 122 (2021) 2353–2428.
65
T.M. Nguyen, D.A. Nicewicz, J. Am. Chem. Soc. 135 (2013) 9588–9591.
66
A.J. Perkowski, D.A. Nicewicz, J. Am. Chem. Soc. 135 (2013) 10334–10337.
67
T.M. Nguyen, N. Manohar, D.A. Nicewicz, Angew. Chem. Int. Ed. 53 (2014) 6198–6201.
68
P.D. Morse, D.A. Nicewicz, Chem. Sci. 6 (2015) 270–274.
69
K.A. Margrey, D.A. Nicewicz, Acc. Chem. Res. 49 (2016) 1997–2006.
70
J.D. Griffin, C.L. Cavanaugh, D.A. Nicewicz, Angew. Chem. Int. Ed. 56 (2017) 2097–2100.
71
T. Chen, M.X. Li, Liu J.Q, Cryst. Growth Des. 18 (2018) 2765–2783.
Appendix
Less
Year 2025 volume 36 Issue 5
PDF
59
34
Cite this Article
BibTeX
Article Info
doi: 10.1016/j.cclet.2024.110253
  • Receive Date：2024-05-20
  • Online Date：2025-10-29
  • Published：2025-05-15
Article Data
Affiliations
History
  • Received：2024-05-20
  • Revised：2024-07-08
  • Accepted：2024-07-15
Affiliations
    a School of Chemistry, Engineering Research Center of Energy Storage Materials and Devices, Ministry of Education, Xi’an Key Laboratory of Sustainable Energy Material Chemistry, Xi’an Jiaotong University, Xi’an 710049, China
    b Department of Chemistry, Key Laboratory for Preparation and Application of Ordered Structural Materials of Guangdong Province, Shantou University, Shantou 515063, China

Corresponding:

*E-mail address: (L. Liu).
References
Share
https://castjournals.cast.org.cn/joweb/ccl/EN/10.1016/j.cclet.2024.110253
Share to
QR

Scan QR to access full text

Cite this article
BibTeX
Citations
表12种不同金属材料的力学参数
科
Family		 属数
Number of
genus		 种数
Number of
species		 占总种数比例
Percentage of
total species (%)		 属
Genus		 种数
Number of
species		 占总种数比例
Percentage of total
species (%)
鹅膏菌科Amanitaceae 2 11 5.26 鹅膏菌属 Amanita 10 4.78
小菇科 Mycenaceae 2 12 5.74 丝盖伞属 Inocybe 5 2.39
多孔菌科 Polyporaceae 8 14 6.70 蜡蘑属 Laccaria 5 2.39
红菇科 Russulaceae 3 23 11.00 小皮伞属 Marasmius 6 2.87
小菇属 Mycena 11 5.26
光柄菇属 Pluteus 5 2.39
红菇属 Russula 17 8.13
栓菌属 Trametes 5 2.39
关闭全屏
  • BibTeX
  • EndNote
  • RefWorks
  • TxT
Links
Articles
Latest Articles
Most Read
Collections
Updates
Events
News
Multimedia
About
About Us
Contact
No. 86 Xueyuan South Road, Haidian District, Beijing
100081
010-62199257
qkjq@cast.org.cn

Copyright © 2025 China Association for Science and Technology. All rights reserved. For all open access content, the relevant licensing terms apply.
Sponsored by the Office of the Leading Group for Cybersecurity and Informatization of CAST, and supported by Science and Technology Review Publishing House