Cu(I)-Catalyzed Coupling of Bis(trimethylsilyl)diazomethane with Terminal Alkynes: A Synthesis of 1,1-Disilyl Allenes

Shuai Xu; Ri Chen; Zihao Fu; Yunpeng Gao; Jianbo Wang

doi:10.1021/acs.joc.8b00651

Cu(I)-Catalyzed Coupling of Bis(trimethylsilyl)diazomethane with Terminal Alkynes: A Synthesis of 1,1-Disilyl Allenes

J Org Chem. 2018 Jun 1;83(11):6186-6192. doi: 10.1021/acs.joc.8b00651. Epub 2018 May 10.

Authors

Shuai Xu¹, Ri Chen¹, Zihao Fu¹, Yunpeng Gao¹, Jianbo Wang^{1

2}

Affiliations

¹ Beijing National Laboratory of Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education , College of Chemistry, Peking University , Beijing 100871 , China.
² The State Key Laboratory of Organometallic Chemistry , Chinese Academy of Sciences , Shanghai 200032 , China.

PMID: 29719960
DOI: 10.1021/acs.joc.8b00651

Abstract

A Cu(I)-catalyzed cross-coupling reaction of terminal alkynes and bis(trimethylsilyl)diazomethane is reported. Mechanistically, the reaction is based on the recently developed cross-coupling reactions through metal-carbene migratory insertion. This reaction provides an efficient synthetic method for 1,1-disilyl allenes. Subsequent transformations of 1,1-disilyl allenes are investigated, which show diverse reactivities of these allenes.

Publication types

Research Support, Non-U.S. Gov't