Copper-catalyzed trifluoromethylation of organic zinc reagents with an electrophilic trifluoromethylating reagent

Chang Sheng Wang; Haoyang Wang; Cheng Yao

doi:10.1039/c5ra02279g

Copper-catalyzed trifluoromethylation of organic zinc reagents with an electrophilic trifluoromethylating reagent

Chang Sheng Wang, Haoyang Wang, Cheng Yao

CAS - Shanghai Institute of Organic Chemistry

Research output: Contribution to journal › Article › peer-review

8 Scopus citations

Abstract

A copper-catalyzed trifluoromethylation of aryl, vinyl and alkyl zinc reagents with Togni's reagent was described. Mechanistic studies indicated that the aryl group is initially transferred from the zinc reagent to hypervalent iodine to form a tri-substituted hypervalent iodine intermediate. Consequent reductive-elimination via a concerted bond-forming step and/or radical pathway from this intermediate generates the trifluoromethylated arenes.

Original language	English
Pages (from-to)	24783-24787
Number of pages	5
Journal	RSC Advances
Volume	5
Issue number	31
DOIs	https://doi.org/10.1039/c5ra02279g
State	Published - 2015

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abstract = "A copper-catalyzed trifluoromethylation of aryl, vinyl and alkyl zinc reagents with Togni's reagent was described. Mechanistic studies indicated that the aryl group is initially transferred from the zinc reagent to hypervalent iodine to form a tri-substituted hypervalent iodine intermediate. Consequent reductive-elimination via a concerted bond-forming step and/or radical pathway from this intermediate generates the trifluoromethylated arenes.",

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AU - Wang, Haoyang

AU - Yao, Cheng

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PY - 2015

Y1 - 2015

N2 - A copper-catalyzed trifluoromethylation of aryl, vinyl and alkyl zinc reagents with Togni's reagent was described. Mechanistic studies indicated that the aryl group is initially transferred from the zinc reagent to hypervalent iodine to form a tri-substituted hypervalent iodine intermediate. Consequent reductive-elimination via a concerted bond-forming step and/or radical pathway from this intermediate generates the trifluoromethylated arenes.

AB - A copper-catalyzed trifluoromethylation of aryl, vinyl and alkyl zinc reagents with Togni's reagent was described. Mechanistic studies indicated that the aryl group is initially transferred from the zinc reagent to hypervalent iodine to form a tri-substituted hypervalent iodine intermediate. Consequent reductive-elimination via a concerted bond-forming step and/or radical pathway from this intermediate generates the trifluoromethylated arenes.

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M3 - 文章

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JO - RSC Advances

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Copper-catalyzed trifluoromethylation of organic zinc reagents with an electrophilic trifluoromethylating reagent

Abstract

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