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

IF 47.3 1区综合性期刊 Q1 MULTIDISCIPLINARY SCIENCES Science Pub Date : 2025-03-06 DOI:10.1126/science.adu6406

Jiawei Sun, Áron Péter, Jiayan He, Jet Tsien, Haoxiang Zhang, David A. Cagan, Benjamin P. Vokits, David S. Peters, Martins S. Oderinde, Michael D. Mandler, Paul Richardson, Doris Chen, Maximilian D. Palkowitz, Nicholas Raheja, Yu Kawamata, Phil S. Baran

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Abstract

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.

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磺酰肼作为自由基交叉偶联的一般氧化还原-中性平台。

磺酰肼是一种稳定的晶体物质，可以通过多种方式获得，包括从腙中短暂获得，以实现羰基化合物的净还原芳基化。我们展示了它们作为多用途自由基前体的效用，例如七个C -C键形成，与活性烯烃，烷基卤化物，氧化还原活性酯，芳基卤化物，烯基卤化物，炔基卤化物和三氟甲基化试剂的氧化还原中性交叉偶联，形成C(sp3)-C(sp3)， C(sp3)-C（sp2）和C(sp3)-C（sp）键。外源性氧化还原（化学，光/电化学）添加剂是不必要的，因为这些官能团具有自由基前体和电子供体的双重作用。均相，水相容的反应条件操作简单，有助于简化合成和温和的后期功能化。

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来源期刊

Science 综合性期刊-综合性期刊

CiteScore

61.10

自引率

0.90%

发文量

审稿时长

2.1 months

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