Dehydrative and Decarboxylative Coupling of Alkynoic Acids with Allylic Alcohols

Ju Qiu; Jingwei Hou; Zuolian Sun; Peizhong Xie

doi:10.1055/a-1750-3080

Synthesis, Table of Contents

Synthesis 2022; 54(12): 2787-2798
DOI: 10.1055/a-1750-3080

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Dehydrative and Decarboxylative Coupling of Alkynoic Acids with Allylic Alcohols

Ju Qiu

,

Jingwei Hou

,

Zuolian Sun

,

Peizhong Xie ∗

Abstract

All articles of this category

Dedicated to Prof. You Huang on the occasion of his 60^th birthday

Abstract

A direct dehydroxylative and decarboxylative coupling between a large number of allylic alcohols and alkynoic acids was realized affording 1,4-enyne motifs in high efficiency. In this reaction, calcium-promoted C–OH bond cleavage was crucial, which facilitated the sequential decarboxylation, and thus enabled the palladium-catalyzed allyl–alkynyl coupling, which occurred in an environmentally benign manner tolerating a wide variety of functional groups. This protocol has been successfully used in preparing anticancer active rooperol derivatives in gram scale.

Key words

dehydrative cross-coupling - C–OH bond cleavage - decarboxylation - 1,4-enynes - green chemistry - cooperative catalysis

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References

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