Ni-catalyzed cross-electrophile coupling between vinyl/aryl and alkyl sulfonates: synthesis of cycloalkenes and modification of peptides. Issue 37 (12th August 2019)

• Record Type: Journal Article
• Authors: Duan, Jicheng; Du, Yun-Fei; Pang, Xiaobo; Shu, Xing-Zhong
• Is Part Of: Chemical science. Volume 10:Issue 37(2019)
• Page Start: 8706
• Page End: 8712
• Publication Date: 2019-08-12
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c9sc03347e
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : We report a reductive coupling between C–O electrophiles, providing an efficient approach to the synthesis of aliphatic cycloalkenes and late-stage 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.