Issue 37, 2019

Ni-catalyzed cross-electrophile coupling between vinyl/aryl and alkyl sulfonates: synthesis of cycloalkenes and modification of peptides

Abstract

We report here the coupling reactions between vinyl/aryl and alkyl C–O electrophiles that can be derived from chemical feedstocks and naturally occurring functional groups. This method provides an efficient approach to the synthesis of a wide range of functionalized, and/or secondary alkyl substituted cycloalkenes. These compounds are difficult to produce by conventional methods. The reaction proceeds with broad substrate scope, and tolerates various functional groups such as alcohol, aldehyde, ketone, ester, amide, alkene, alkyne, heterocycles, organotin and organosilicon compounds. The synthetic utility of this method has been demonstrated by providing facile access to important building blocks. We also demonstrated the possibility to apply this method for late-stage modification of peptides. A broad range of functionalized alkyl groups could be selectively introduced into tyrosine in peptides via C–C bond formation, which has been a challenge to the existing procedures.

Graphical abstract: Ni-catalyzed cross-electrophile coupling between vinyl/aryl and alkyl sulfonates: synthesis of cycloalkenes and modification of peptides

Supplementary files

Article information

Article type
Edge Article
Submitted
06 Jul 2019
Accepted
04 Aug 2019
First published
05 Aug 2019
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2019,10, 8706-8712

Ni-catalyzed cross-electrophile coupling between vinyl/aryl and alkyl sulfonates: synthesis of cycloalkenes and modification of peptides

J. Duan, Y. Du, X. Pang and X. Shu, Chem. Sci., 2019, 10, 8706 DOI: 10.1039/C9SC03347E

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