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"Sandwich" Diimine-Copper Catalysts for C-H Functionalization by Carbene Insertion.

ABSTRACT: We report here "sandwich" diimine-copper(I) catalysts for C(sp³ )-H bond functionalization. Reactions of alkanes and ethers with trimethylsilyldiazomethane, ethyl diazoacetate, and trifluoromethyl-diazomethane have been demonstrated. We also report C(sp³ )-H bond methylation, benzylation, and diphenylmethylation by diazomethane, aryldiazomethanes, and diphenyldiazomethane. These reactions are rare examples of base-metal catalyzed, intermolecular C(sp³ )-H functionalizations by employing unactivated diazo compounds. Electrophilicity and unique steric environment of "sandwich"-copper catalysts are likely reasons for their catalytic efficiency.

SUBMITTER: Klimovica K

PROVIDER: S-EPMC9329213 | biostudies-literature | 2022 Aug

REPOSITORIES: biostudies-literature

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"Sandwich" Diimine-Copper Catalysts for C-H Functionalization by Carbene Insertion.

Klimovica Kristine K Heidlas Julius X JX Romero Irvin I Le Thanh V TV Daugulis Olafs O

Angewandte Chemie (International ed. in English) 20220610 31

We report here "sandwich" diimine-copper(I) catalysts for C(sp3 )-H bond functionalization. Reactions of alkanes and ethers with trimethylsilyldiazomethane, ethyl diazoacetate, and trifluoromethyl-diazomethane have been demonstrated. We also report C(sp3 )-H bond methylation, benzylation, and diphenylmethylation by diazomethane, aryldiazomethanes, and diphenyldiazomethane. These reactions are rare examples of base-metal catalyzed, intermolecular C(sp3 )-H functio ...[more]

PMID: 35594167

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