BINAP-Accelerated\nCopper-Mediated Photochemical Late-Stage\nTrifluoromethylation of Arenes

Site-selective and late-stage C–H trifluoromethylation\n(including\npentafluoroethylation) of arylthianthrenium salts using <i>in\nsitu</i> generated CuCF<sub>3</sub> from Ruppert–Prakash\nreagent under visible light was found to be significantly accelerated\nby a catalytic amount of <i>rac</i>-BINAP, allowing the\nreaction to complete within 15 min under very mild conditions without\nusing any additional photoredox catalysts. The process showed a broad\nsubstrate scope, high efficiency, and excellent regioselectivity,\nwhich holds the promise to accelerate the discovery of fluorinated\nmedicinal compounds.

Publication Details

Journal
Figshare
Published
2024-12-05
DOI
https://doi.org/10.1021/acs.orglett.4c04092.s001
Primary Topic
Fluorine in Organic Chemistry
Type
article
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0.00
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article

BINAP-Accelerated\nCopper-Mediated Photochemical Late-Stage\nTrifluoromethylation of Arenes

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Fluorine in Organic Chemistry
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BINAP-Accelerated\nCopper-Mediated Photochemical Late-Stage\nTrifluoromethylation of Arenes

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Abstract

Site-selective and late-stage C–H trifluoromethylation\n(including\npentafluoroethylation) of arylthianthrenium salts using <i>in\nsitu</i> generated CuCF<sub>3</sub> from Ruppert–Prakash\nreagent under visible light was found to be significantly accelerated\nby a catalytic amount of <i>rac</i>-BINAP, allowing the\nreaction to complete within 15 min under very mild conditions without\nusing any additional photoredox catalysts. The process showed a broad\nsubstrate scope, high efficiency, and excellent regioselectivity,\nwhich holds the promise to accelerate the discovery of fluorinated\nmedicinal compounds.

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Openalex Percentile: Top 63%
Fluorine in Organic Chemistry
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BINAP-Accelerated\nCopper-Mediated Photochemical Late-Stage\nTrifluoromethylation of Arenes · Figshare (2024) | TGRS Research Map | TGRS