A photoinduced three-component anti-Markovnikov chloroalkynylation of unactivated alkenes is enabled by proton-coupled electron transfer (PCET) using bench-stable HCl and alkynyl sulfones. A neutral acridine photocatalyst promotes cascade radical addition/fragmentation under mild conditions, delivering highly regioselective products otherwise difficult to access. The method accommodates diverse unactivated alkenes, including alkyl-substituted, 1,1-disubstituted, and drug-like derivatives. Diverse downstream derivatizations highlight the synthetic utility of these chloroalkyne building blocks.
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Yun-Kai Wang
Xinyu Yang
Jin Zhou
Organic Letters
Hefei University of Technology
Hefei University
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Wang et al. (Wed,) studied this question.
www.synapsesocial.com/papers/69d896566c1944d70ce07ad6 — DOI: https://doi.org/10.1021/acs.orglett.6c00775
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