Pentafluorosulfanylation\nof Acrylamides: The Synthesis\nof SF<sub>5</sub>‑Containing Isoquinolinediones with SF<sub>5</sub>Cl

We\ndisclose herein an efficient and facile method for the synthesis\nof SF<sub>5</sub>-containing isoquinolinediones with an all-carbon\nquaternary stereocenter via intramolecular pentafluorosulfanylation\nof acrylamides using SF<sub>5</sub>Cl as a pentafluorosulfanylation\nreagent. The protocol proceeds under mild reaction conditions and\nenjoys a broad substrate scope, wide functional group compatibility,\nand high atom- and step-economy. A radical mechanism involving the\nSF<sub>5</sub> radical cascade addition/cyclization of acrylamides\nis proposed.

Publication Details

Journal
Figshare
Published
2024-10-24
DOI
https://doi.org/10.1021/acs.joc.4c02181.s001
Primary Topic
Fluorine in Organic Chemistry
Type
article
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article

Pentafluorosulfanylation\nof Acrylamides: The Synthesis\nof SF5‑Containing Isoquinolinediones with SF5Cl

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Fluorine in Organic Chemistry
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Pentafluorosulfanylation\nof Acrylamides: The Synthesis\nof SF5‑Containing Isoquinolinediones with SF5Cl

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Abstract

We\ndisclose herein an efficient and facile method for the synthesis\nof SF<sub>5</sub>-containing isoquinolinediones with an all-carbon\nquaternary stereocenter via intramolecular pentafluorosulfanylation\nof acrylamides using SF<sub>5</sub>Cl as a pentafluorosulfanylation\nreagent. The protocol proceeds under mild reaction conditions and\nenjoys a broad substrate scope, wide functional group compatibility,\nand high atom- and step-economy. A radical mechanism involving the\nSF<sub>5</sub> radical cascade addition/cyclization of acrylamides\nis proposed.

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Fluorine in Organic Chemistry
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Pentafluorosulfanylation\nof Acrylamides: The Synthesis\nof SF<sub>5</sub>‑Containing Isoquinolinediones with SF<sub>5</sub>Cl · Figshare (2024) | TGRS Research Map | TGRS