Photocatalytic access to aromatic keto sulfonyl fluorides from vinyl fluorosulfates

We present herein an efficient photocatalytic transformation of vinyl fluorosulfates to aromatic β-keto sulfonyl fluorides with 1 mol% of iridium catalyst under the irradiation of 3 W blue LEDs. Preliminary mechanistic studies proposed a direct radical fragmentation and recombination of vinyl fluoro...

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Veröffentlicht in:Organic Chemistry Frontiers 2022-06, Vol.9 (13), p.3540-3545
Hauptverfasser: Cui, Jianchao, Ke, Sen, Zhao, Jia, Wu, Shufeng, Luo, Wencheng, Xu, Shinuo, Su, Xiaolong, Li, Yi
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Sprache:eng
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Zusammenfassung:We present herein an efficient photocatalytic transformation of vinyl fluorosulfates to aromatic β-keto sulfonyl fluorides with 1 mol% of iridium catalyst under the irradiation of 3 W blue LEDs. Preliminary mechanistic studies proposed a direct radical fragmentation and recombination of vinyl fluorosulfates through a free fluorosulfonyl radical (FSO 2 ˙ ). This methodology provides a facile approach to aromatic β-keto sulfonyl fluorides, featuring sustainable conditions and a broad substrate scope (32 examples) with 33%–90% isolated yields.
ISSN:2052-4129
2052-4110
2052-4129
2052-4110
DOI:10.1039/D2QO00416J