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Regioselective control using a catalyst switch in the reaction of diarylmethyl chlorides with allyltributylstannane

Release Time:2019-03-09  Hits:

Indexed by: Journal Article

Date of Publication: 2010-08-07

Journal: TETRAHEDRON

Included Journals: Scopus、SCIE

Volume: 66

Issue: 32

Page Number: 6013-6018

ISSN: 0040-4020

Key Words: Regioselective control; Catalyst switch; Diarylmethyl chloride; Allyltributylstannane

Abstract: Regioselective control in the reaction of diarylmethyl chlorides 5a with allyltributyltin is described. The reaction pathway (allylative dearomatization vs cross-coupling) can be easily controlled using different catalysts. When reactions are performed in the presence of Pd(2)(dba)(3) and PPh(3), allylative dearomatization proceeds to provide satisfactory yield of the desired products. However, when Cy(3)P center dot HBF(4) is employed as a catalyst instead of palladium, a Stille-type cross-coupling reaction takes place exclusively to give excellent yields of the corresponding products. (c) 2010 Elsevier Ltd. All rights reserved.

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