Understanding cyclic(alkyl)(amino)carbene–copper complex catalysed N–H and O–H bond addition to electron deficient olefins

Abstract

The hydroamination of electron-deficient olefins was carried out using the (CAAC)Cu–Cl (CAAC = cyclic (alkyl)(amino)carbene) catalyst with an excellent yield at room temperature and under an open atmosphere. Furthermore, the catalyst shows excellent efficiency in the hydroaryloxylation and hydroalkoxylation of alkenes under mild conditions. The efficiency of the catalyst was tested for a wide range of substrates with different electronic and steric functionalities. Detailed computational studies have been carried out to understand the mechanism of these Cu(I) catalyzed reactions, which revealed that the reaction proceeds via either a four-membered or a six-membered cyclic transition state containing the copper ion.

Graphical abstract: Understanding cyclic(alkyl)(amino)carbene–copper complex catalysed N–H and O–H bond addition to electron deficient olefins

Supplementary files

Article information

Article type
Communication
Submitted
15 Oct 2022
Accepted
23 Nov 2022
First published
24 Nov 2022

Chem. Commun., 2023, Advance Article

Understanding cyclic(alkyl)(amino)carbene–copper complex catalysed N–H and O–H bond addition to electron deficient olefins

A. Tyagi, S. Mondal, Anmol, V. Tiwari, T. Karmakar and S. Kundu, Chem. Commun., 2023, Advance Article , DOI: 10.1039/D2CC05613E

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