Issue 1, 2023

Recent development of allyl–allyl cross-coupling and its application in natural product synthesis

Abstract

The allyl–allyl cross-coupling reaction is one of the most important cross-coupling reactions as it provides a practical synthetic route for the direct construction of 1,5-dienes, which are abundant in terpenes, and are significant building blocks in chemical synthesis. The transition metal-catalyzed cross-coupling has the power to generate synthetically important 1,5-dienes from an allylic nucleophile and allylic electrophile. Catalysts derived from different metals, including Pd, Ni, Cu, Ir etc. are extensively studied and show excellent regio- and enantioselective control. Moreover, this strategy has been successfully applied in stereoselective total syntheses of a number of complex natural products. Major developments have been observed over the past decade in the allyl–allyl cross-coupling strategy, and the application of a new tool for regio-and enantioselective C–C bond formation to form the 1,5-diene has revolutionized synthetic chemistry. The present Short Review summarises the most significant advancements that have provided access to a wide variety of branched/and linear 1,5 dienes of synthetic and pharmaceutical importance during the past decade. To the best of our knowledge, this is the first review on the allyl–allyl cross-coupling reaction.

Graphical abstract: Recent development of allyl–allyl cross-coupling and its application in natural product synthesis

Article information

Article type
Review Article
Submitted
06 jul 2022
Accepted
13 okt 2022
First published
15 okt 2022

Org. Chem. Front., 2023,10, 267-281

Recent development of allyl–allyl cross-coupling and its application in natural product synthesis

V. Ravichandiran and A. Jana, Org. Chem. Front., 2023, 10, 267 DOI: 10.1039/D2QO01078J

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