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Synthesis 2022; 54(12): 2787-2798
DOI: 10.1055/a-1750-3080
DOI: 10.1055/a-1750-3080
feature
Dehydrative and Decarboxylative Coupling of Alkynoic Acids with Allylic Alcohols
We gratefully acknowledge financial support from the National Natural Science Foundation of China (21702108), the Natural Science Foundation of Jiangsu Province, China (BK20211257, BK20160977), and the Six Talent Peaks Project in Jiangsu Province (YY-033).
Dedicated to Prof. You Huang on the occasion of his 60th 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 catalysisSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1750-3080.
- Supporting Information
Publication History
Received: 11 November 2021
Accepted after revision: 25 January 2022
Accepted Manuscript online:
25 January 2022
Article published online:
08 March 2022
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