RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2024; 56(09): 1393-1400
DOI: 10.1055/a-2240-5349
DOI: 10.1055/a-2240-5349
paper
Copper-Catalyzed Enantioselective Radical Esterification of Propargylic C–H Bonds
This work was supported by the National Natural Science Foundation of China (22225107, 22301302, 22001251) and the China Postdoctoral Science Foundation (2023M733500, BX20230366).
Abstract
The copper-catalyzed enantioselective radical esterification of propargylic C–H bonds with tert-butyl peroxybenzoate (TBPB) as an oxidizing agent and an oxygenated nucleophile is reported. This variant of the Kharasch–Sosnovsky oxidation allows for the asymmetric esterification of open-chain carbon radicals without excessive amounts of alkyne substrates under mild reaction conditions, achieving a one-step conversion of simple alkynes into chiral propargylic esters.
Key words
enantioselective esterification - propargylic - Kharasch–Sosnovsky oxidation - copper catalysis - radicalSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2240-5349.
- Supporting Information
Publikationsverlauf
Eingereicht: 12. Dezember 2023
Angenommen nach Revision: 08. Januar 2024
Accepted Manuscript online:
08. Januar 2024
Artikel online veröffentlicht:
08. Februar 2024
© 2024. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1a Jiao ZW, Zhang SY, He C, Tu YQ, Wang SH, Zhang FM, Zhang YQ, Li H. Angew. Chem. Int. Ed. 2012; 51: 8811
- 1b Zheng C, You S.-L. RSC Adv. 2014; 4: 6173
- 1c Seitz LC, Dickens CF, Nishio K, Hikita Y, Montoya J, Doyle A, Kirk C, Vojvodic A, Hwang HY, Norskov JK, Jaramillo TF. Science 2016; 353: 1011
- 1d Stockerl S, Mancheño OG. Org. Chem. Front. 2016; 3: 277
- 1e Yang S.-D, Cheng M.-X. Synlett 2016; 28: 159
- 1f Vasilopoulos A, Zultanski SL, Stahl SS. J. Am. Chem. Soc. 2017; 139: 7705
- 1g Zhang W, Chen P, Liu G. J. Am. Chem. Soc. 2017; 139: 7709
- 1h Thongpaen J, Manguin R, Basle O. Angew. Chem. Int. Ed. 2020; 59: 10242
- 1i Yang K, Song M, Liu H, Ge H. Chem. Sci. 2020; 11: 12616
- 1j Fan W, Zhao X, Deng Y, Chen P, Wang F, Liu G. Angew. Chem. Int. Ed. 2022; 144: 21674
- 1k Xu P, Fan W, Chen P, Liu G. J. Am. Chem. Soc. 2022; 144: 13468
- 1l Zhang Z, Chen P, Liu G. Chem. Soc. Rev. 2022; 51: 1640
- 1m Deng Y, Lu R, Chen P, Liu G. Chem. Commun. 2023; 59: 4656
- 2a Kharasch MS, Sosnovsky G. J. Am. Chem. Soc. 1995; 80: 756
- 2b Kharasch MS, Sosnovsky G, Yang NC. J. Am. Chem. Soc. 1995; 81: 5819
- 3 Gokhale AS, Minidis AB. E, Pfaltz A. Tetrahedron Lett. 1995; 36: 1831
- 4 Andrus MB, Argade AB, Chen X, Pamment MG. Tetrahedron Lett. 1995; 36: 2945
- 5 Kawasaki K, Tsumura S, Katsuki T. Synlett 1995; 1245
- 6a Kohmura Y, Katsuki T. Synlett 1999; 1231
- 6b Kohmura Y, Katsuki T. Tetrahedron Lett. 2000; 41: 3941
- 6c Eames J, Watkinson M. Angew. Chem. Int. Ed. 2001; 40: 3567
- 6d Andrus MB, Lashley JC. Tetrahedron 2002; 58: 845
- 6e Le Bras J, Muzart J. Tetrahedron: Asymmetry 2003; 14: 1911
- 6f Clark JS, Clarke M.-R, Clough J, Blake AJ, Wilson C. Tetrahedron Lett. 2004; 45: 9447
- 6g Boyd DR, Sharma ND, Sbircea L, Murphy D, Belhocine T, Malone JF, James SL, Allen CC, Hamilton JT. Chem. Commun. 2008; 5535
- 6h Mayoral JA, Rodriguez-Rodriguez S, Salvatella L. Chem. Eur. J. 2008; 14: 9274
- 6i Aldea L, Delso I, Hager M, Glos M, García JI, Mayoral JA, Reiser O. Tetrahedron 2012; 68: 3417
- 6j Aldea L, Garcia JI, Mayoral JA. Dalton Trans. 2012; 41: 8285
- 6k Guerra F, García-Cabeza A, Moreno-Dorado F, Ortega M. Synthesis 2016; 48: 2323
- 6l Nozawa-Kumada K, Saga S, Matsuzawa Y, Hayashi M, Shigeno M, Kondo Y. Chem. Eur. J. 2020; 26: 4496
- 7a Nilsson BM, Vargas HM, Hacksell U. J. Med. Chem. 1992; 35: 2787
- 7b McLaughlin NP, Butler E, Evans P, Brunton NP, Koidis A, Rai DK. Tetrahedron 2010; 66: 9681
- 7c Hinds L, Kenny O, Hossain MB, Walsh D, Sheehy E, Evans P, Gaffney M, Rai DK. J. Agric. Food Chem. 2017; 65: 7186
- 8 Lu R, Yang T, Chen X, Fan W, Chen P, Lin Z, Liu G. J. Am. Chem. Soc. 2021; 143: 14451
- 9a Wang F, Wang D, Zhou Y, Liang L, Lu R, Chen P, Lin Z, Liu G. Angew. Chem. Int. Ed. 2018; 57: 7140
- 9b Zhu X, Deng W, Chiou MF, Ye C, Jian W, Zeng Y, Jiao Y, Ge L, Li Y, Zhang X, Bao H. J. Am. Chem. Soc. 2019; 141: 548
- 9c Zeng Y, Chiou MF, Zhu X, Cao J, Lv D, Jian W, Li Y, Zhang X, Bao H. J. Am. Chem. Soc. 2020; 142: 18014
- 9d Li Y, Bao H. Chem. Sci. 2022; 13: 8491
- 10a Chen J, Liang YJ, Wang PZ, Li GQ, Zhang B, Qian H, Huan XD, Guan W, Xiao WJ, Chen JR. J. Am. Chem. Soc. 2021; 143: 13382
- 10b Wang PZ, Wu X, Cheng Y, Jiang M, Xiao WJ, Chen JR. Angew. Chem. Int. Ed. 2021; 60: 22956
- 10c Zhu X, Jian W, Huang M, Li D, Li Y, Zhang X, Bao H. Nat. Commun. 2021; 12: 6670
- 10d Nie Z, Chiou MF, Cui J, Qu Y, Zhu X, Jian W, Xiong H, Li Y, Bao H. Angew. Chem. Int. Ed. 2022; 61: e202202077
- 10e Wang PZ, Liang YJ, Wu X, Guan W, Xiao WJ, Chen JR. ACS Catal. 2022; 12: 10925
- 10f Xue M, Cui J, Zhu X, Wang F, Lv D, Nie Z, Li Y, Bao H. Angew. Chem. Int. Ed. 2023; 62: e202304275
- 11 Clark JS, Tolhurst KF, Taylor M, Swallow S. Tetrahedron Lett. 1998; 39: 4913
- 12 Wang H, Qian H, Zhang J, Ma S. J. Am. Chem. Soc. 2022; 144: 12619
- 13 Ghosh N, Nayak S, Sahoo AK. J. Org. Chem. 2011; 76: 500