Sulfonyl hydrazides as a general redox-neutral platform for radical cross-coupling

• 成果类型: Article
• 署名作者: Sun, Jiawei; Peter, Aron; He, Jiayan; Tsien, Jet; Zhang, Haoxiang; Cagan, David A.; Vokits, Benjamin P.; Peters, David S.; Oderinde, Martins S.; Mandler, Michael D.; Richardson, Paul; Chen, Doris; Palkowitz, Maximilian D.; Raheja, Nicholas; Kawamata, Yu; Baran, Phil S.
• 署名单位: Scripps Research Institute; Bristol-Myers Squibb; Bristol-Myers Squibb; Bristol-Myers Squibb; Pfizer; Pfizer USA; Bristol-Myers Squibb
• 刊物名称: SCIENCE
• ISSN/ISSBN: 0036-13579
• DOI: 10.1126/science.adu6406
• 发表日期: 2025-03-28
• 页码: 1377-1383
• 关键词: active esters; carbon; trifluoromethylation

摘要

Sulfonyl hydrazides are stable and usually crystalline substances that can be accessed in a variety of ways, including transiently from hydrazones, to achieve a net reductive arylation of carbonyl compounds. We show their utility as versatile radical precursors, as exemplified with seven C-C bond-forming, redox-neutral cross-couplings with activated olefins, alkyl halides, redox-active esters, aryl halides, alkenyl halides, alkynyl halides, and a trifluoromethylating reagent, to forge C(sp3)-C(sp3), C(sp3)-C(sp2), and C(sp3)-C(sp) bonds. Exogenous redox (chemical, photo/electrochemical) additives are not necessary because these functional groups serve the dual role of radical precursor and electron donor. The homogeneous, water-compatible reaction conditions are operationally simple and contribute to streamlining synthesis and mild late-stage functionalization.