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Angew Chem Int Ed Engl. 2016 Feb 24;55(9):3140-3. doi: 10.1002/anie.201510354. Epub 2016 Jan 28.

Copper-Catalyzed Borylcupration of Allenylsilanes.

Author information

1
Shanghai Key Laboratory of Green Chemistry and Chemical Process, Department of Chemistry, East China Normal University, 3663 North Zhongshan Lu, Shanghai, 200062, P. R. China.
2
Department of Chemistry, Fudan University, 220 Handan Lu, Shanghai, 200433, P. R. China.
3
Department of Chemistry, Fudan University, 220 Handan Lu, Shanghai, 200433, P. R. China. masm@sioc.ac.cn.
4
State Key Laboratory of Organometallic Chemistry, Shanghai, Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032, P. R. China. masm@sioc.ac.cn.

Abstract

A highly regio- and stereoselective copper-catalyzed borylcupration of 1,2-allenylsilanes affords an unexpected regioreversed allylic boronate bearing an extra C-Si bond at the 3-position, with a thermodynamically disfavored Z geometry. Such stereodefined allylic boronates containing an extra alkenyl silane moiety are very useful organodimetallic reagents for organic synthesis.

KEYWORDS:

allylic compounds; boron; copper; regioselectivity; stereoselectivity

PMID:
26821774
DOI:
10.1002/anie.201510354

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