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

Abstract

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(sp3)–C(sp3) 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. The synthesis of alkenes from carboxylic acids, alcohols and alkanes is a formidable challenge owing to their inherent differences in reactivity. Now the one-pot conversion of these building blocks into alkenes is reported through an integrated photochemical strategy using a phenyl vinyl ketone as the olefination reagent.