Work

“Sandwich” Diimine‐Copper Catalysts for C−H Functionalization by Carbene Insertion

Year: 2022

Type: article

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.

Source: Angewandte Chemie International Edition

DOI: 10.1002/anie.202200334

Authors: Kristine Klimovica, Julius X. Heidlas, Irvin Romero, Thanh V. Le, Olafs Daugulis

Institution: University of Houston

Language: English

Topic: Cyclopropane Reaction Mechanisms

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: Welch Foundation, National Institute of General Medical Sciences

Awards: G2854228422, New Methods for Direct Carbon-Hydrogen Bond Functionalization