Copper-Catalyzed Reaction of 2,3-Allenols with Silylzinc Reagents: Access to 2-Silyl-1,3-butadienes

Guang-Li Xu; Yu-Tong Duan; Zhong-Xia Wang

doi:10.1021/acs.orglett.2c03041

Copper-Catalyzed Reaction of 2,3-Allenols with Silylzinc Reagents: Access to 2-Silyl-1,3-butadienes

Org Lett. 2022 Nov 4;24(43):7934-7938. doi: 10.1021/acs.orglett.2c03041. Epub 2022 Oct 21.

Authors

Guang-Li Xu¹, Yu-Tong Duan¹, Zhong-Xia Wang¹

Affiliation

¹ CAS Key Laboratory of Soft Matter Chemistry and Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, P. R. China.

PMID: 36268997
DOI: 10.1021/acs.orglett.2c03041

Abstract

Reaction of 2,3-allenols with PhMe₂SiZnCl or Ph₂MeSiZnCl under catalysis of IPrCuCl or SIPrCuCl was carried out, affording 2-silyl-1,3-butadienes. Secondary and tertiary 2,3-allenols could be used as coupling partners. Reaction of secondary 2,3-allenols gave (E)-2-silyl-1,3-butadienes as the only products.