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γ-Selective Allylation of (E)-Alkenylzinc Iodides Prepared by Reductive Coupling of Arylacetylenes with Alkyl Iodides.

Authors :
Zhurkin, Fedor E.
Xile Hu
Source :
Journal of Organic Chemistry. 7/1/2016, Vol. 81 Issue 13, p5795-5802. 8p.
Publication Year :
2016

Abstract

The first examples of Cu-catalyzed γ-selective allylic alkenylation using organozinc reagents are reported. (E)-Alkenylzinc iodides were prepared by Fe-catalyzed reductive coupling of terminal arylalkynes with alkyl iodides. In the presence of a copper catalyst, these reagents reacted with allylic bromides derived from Morita-Baylis-Hillman alcohols to give 1,4-dienes in high yields. The reactions are highly γ-selective (generally γ/α > 49:1) and tolerate a wide range of functional groups such as ester, cyano, keto, and nitro. [ABSTRACT FROM AUTHOR]

Details

Language :
English
ISSN :
00223263
Volume :
81
Issue :
13
Database :
Academic Search Index
Journal :
Journal of Organic Chemistry
Publication Type :
Academic Journal
Accession number :
116642764
Full Text :
https://doi.org/10.1021/acs.joc.6b01306