Cu(II)-catalyzed allylic silylation of Morita-Baylis-Hillman alcohols via dual activation of Si-B bond and hydroxyl group

Qing-Qing Xuan; Neng-Jun Zhong; Chuan-Li Ren; Li Liu; Dong Wang; Yong-Jun Chen; Chao-Jun Li

doi:10.1021/jo4016419

Cu(II)-catalyzed allylic silylation of Morita-Baylis-Hillman alcohols via dual activation of Si-B bond and hydroxyl group

J Org Chem. 2013 Nov 1;78(21):11076-81. doi: 10.1021/jo4016419. Epub 2013 Oct 24.

Authors

Qing-Qing Xuan¹, Neng-Jun Zhong, Chuan-Li Ren, Li Liu, Dong Wang, Yong-Jun Chen, Chao-Jun Li

Affiliation

¹ Beijing National Laboratory for Molecular Sciences (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences , Beijing 100190, China.

PMID: 24093603
DOI: 10.1021/jo4016419

Abstract

The reaction of Morita-Baylis-Hillman (MBH) alcohols with Me2PhSiBpin under the catalysis of Cu(OTf)2/pyridine in methanol has been developed. The direct silylation of allylic alcohols via dual activation of the Si-B bond and the hydroxyl group of the MBH alcohol provides an efficient and convenient method for the synthesis of functionalized allylsilanes.

Publication types

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

MeSH terms

Alcohols / chemistry*
Catalysis
Mesylates / chemistry*
Molecular Structure
Silanes / chemical synthesis*
Silanes / chemistry*
Stereoisomerism

Substances

Alcohols
Mesylates
Silanes
trifluoromethanesulfonic acid