Decarboxylative and dehydrative coupling of dienoic acids and pentadienyl alcohols to form 1,3,6,8-tetraenes

Decarboxylative and dehydrative coupling of dienoic acids and pentadienyl alcohols to form 1,3,6,8-tetraenes

Dienoic acids and pentadienyl alcohols are coupled in a decarboxylative and dehydrative manner at ambient temperature using Pd(0) catalysis to generate 1,3,6,8-tetraenes. Contrary to related decarboxylative coupling reactions, an anion-stabilizing group is not required adjacent to the carboxyl group...

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Bibliographic Details
Main Authors: Ghina’a I. Abu Deiab, Mohammed H. Al-Huniti, I. F. Dempsey Hyatt, Emma E. Nagy, Kristen E. Gettys, Sommayah S. Sayed, Christine M. Joliat, Paige E. Daniel, Rupa M. Vummalaneni, Andrew T. Morehead Jr, Andrew L. Sargent, Mitchell P. Croatt
Format: Article
Language:English
Published: Beilstein-Institut 2017-02-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
decarboxylation
diene
dienoate
palladium
pentadienyl
tetraene
Online Access:https://doi.org/10.3762/bjoc.13.41
Description
Summary:Dienoic acids and pentadienyl alcohols are coupled in a decarboxylative and dehydrative manner at ambient temperature using Pd(0) catalysis to generate 1,3,6,8-tetraenes. Contrary to related decarboxylative coupling reactions, an anion-stabilizing group is not required adjacent to the carboxyl group. Of mechanistic importance, it appears that both the diene of the acid and the diene of the alcohol are required for this reaction. To further understand this reaction, substitutions at every unique position of both coupling partners was examined and two potential mechanisms are presented.
ISSN:1860-5397

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