Access to functionalized alkynylcyclopropanes via reductive radical-polar crossover-based reactions of 1, 3-enynes with alkyl radicals. Issue 4 (5th January 2023)

• Record Type: Journal Article
• Authors: Zhang, Beibei; Luo, Junfei; Fang, Yewen
• Is Part Of: Organic & biomolecular chemistry. Volume 21:Issue 4(2023)
• Page Start: 732
• Page End: 737
• Publication Date: 2023-01-05
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d2ob02155b
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Using SET reduction as the key process, functionalized alkynylcyclopropanes could be accessed via the reactions of 1, 3-enynes with alkyl radicals enabled by photoredox or nickel catalysis. Abstract : Herein, using a single-electron-transfer reduction-based radical-polar crossover process as a strategy, protocols dealing with the preparation of functionalized alkynylcyclopropanes have been successfully developed via the reactions of 1, 3-enynes with alkyl radicals. In addition to redox-neutral photocatalysis, nickel catalysis with zinc as the reductant is also an alternative to enable reactions of 1, 3-enynes with redox-active N -hydroxyphthalimide esters. The synthetic application of alkynylcyclopropane has also been demonstrated.