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- Title
Photocatalytic [3+2] Cycloaddition of Alkyl/aryl Iodides and Internal Alkynes by Merging Halogen and Hydrogen Atom Transfer.
- Authors
Gu, Zhenyu; Jia, Rong; Zeng, Tianqing; Zheng, Hanliang; Zhu, Gangguo
- Abstract
Comprehensive Summary: A visible light photocatalytic [3+2] cycloaddition of alkynes with readily accessible organic iodides as the C3 synthon is developed herein. By merging halogen atom transfer (XAT) and hydrogen atom transfer (HAT), alkyl/aryl iodides serve as a formal diradical precursor and add across C‐C triple bonds to deliver a number of functionalized cyclopentanes in moderate to high yields with exceptional regio‐ and diastereoselectivity. A reductive radical‐polar crossover mechanism, involving the cascade XAT, radical addition, 1,5‐HAT, polar effect‐promoted 5‐endo annulation, single electron transfer (SET) reduction, and protonation, may account for this unprecedented dehalogenative [3+2] cycloaddition. This work not only expands the repertoire of the traditional RATC methodology, but also provides a robust platform for the expedient assembly of cyclopentanes, a valuable structural motif in the realms of medicinal chemistry and material sciences.
- Subjects
ABSTRACTION reactions; MATERIALS science; ARYL iodides; CHARGE exchange; PHARMACEUTICAL chemistry
- Publication
Chinese Journal of Chemistry, 2024, Vol 42, Issue 19, p2329
- ISSN
1001-604X
- Publication type
Article
- DOI
10.1002/cjoc.202400366