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May 15, 2026The Journal of Organic Chemistry0 citations

Three-Component Carbopentafluorosulfanylation of Activated Alkenes with SF 5 Cl and Quinoxalin-2(1 H )-ones

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XTXinqiang TanZHZiyou HaoXinxiang Medical UniversityHWHuiping WangJiangnan University

Key Points

  • This research demonstrates a novel method for synthesizing compounds with quinoxalin-2(1H)-one and SF5 groups using a three-component reaction.
  • Direct reaction of styrene with SF5Cl and quinoxalin-2(1H)-ones
  • Utilization of mild reaction conditions and broad substrate scope
  • Synthesis confirmed by production of complex natural products and pharmaceuticals
  • Successful synthesis of high-value compounds with quinoxalin-2(1H)-one and SF5 moieties
  • Demonstrated good functional group tolerance
  • Proposed mechanism involves SF5 radical addition to C=C double bond followed by capture of quinoxalin-2(1H)-one

Abstract

For the first time, we herein report an efficient and general method to access a series of high-value compounds concurrently containing quinoxalin-2(1H)-one and SF5 moieties through a three-component reaction strategy by direct carbopentafluorosulfanylation of styrene with SF5Cl and quinoxalin-2(1H)-ones. The protocol enjoys mild reaction conditions, good functional group tolerance, and broad substrate scope, which was further evidenced by the synthesis of complex natural products and pharmaceuticals. A plausible mechanism involving SF5 radical addition to the C = C double bond, followed by capture of quinoxalin-2(1H)-one, is proposed.

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Cite This Study

Tan et al. (2026) studied this question.

synapsesocial.com/papers/6a06b7a1e7dec685947aa685https://doi.org/10.1021/acs.joc.6c00066
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