Modular alkene synthesis from carboxylic acids, alcohols and alkanes via integrated photocatalysis.

Nat Chem

Joint School of National University of Singapore and Tianjin University, International Campus of Tianjin University, Binhai New City, P. R. China.

Published: November 2024

Alkenes serve as versatile building blocks in diverse organic transformations. Despite notable advancements in olefination methods, a general strategy for the direct conversion of carboxylic acids, alcohols and alkanes into alkenes remains a formidable challenge owing to their inherent reactivity disparities. Here we demonstrate an integrated photochemical strategy that facilitates a one-pot conversion of these fundamental building blocks into alkenes through a sequential C(sp)-C(sp) bond formation-fragmentation process, utilizing an easily accessible and recyclable phenyl vinyl ketone as the 'olefination reagent'. This practical method not only offers an unparalleled paradigm for accessing value-added alkenes from abundant and inexpensive starting materials but also showcases its versatility through various complex scenarios, including late-stage on-demand olefination of multifunctional molecules, chain homologation of acids and concise syntheses of bioactive molecules. Moreover, initiating from carboxylic acids, alcohols and alkanes, this protocol presents a complementary approach to traditional olefination methods, making it a highly valuable addition to the research toolkit for alkene synthesis.

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Source
http://dx.doi.org/10.1038/s41557-024-01642-6DOI Listing

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