A Simple and Fast Access to Phosphine-Substituted Copper(I)-Carbene Complexes via C=Se Bond Cleavage Reaction

Sabari Veerapathiran; Ganesan Prabusankar

doi:10.1002/asia.202300217

A Simple and Fast Access to Phosphine-Substituted Copper(I)-Carbene Complexes via C=Se Bond Cleavage Reaction

Chem Asian J. 2023 Jun 1;18(11):e202300217. doi: 10.1002/asia.202300217. Epub 2023 Apr 27.

Authors

Sabari Veerapathiran¹, Ganesan Prabusankar¹

Affiliation

¹ Organometallics and Materials Chemistry Lab, Department of Chemistry, Indian Institute of Technology Hyderabad, Kandi, Sangareddy, Telangana, 502285, India.

PMID: 37067916
DOI: 10.1002/asia.202300217

Abstract

Phosphine coordinated copper(I)-N-heterocyclic carbene complexes have emerged as an efficient material in catalysis and light-emitting applications. In this study, a gentle and sustainable approach to the copper(I)-carbene phosphine complexes is reported through an efficient C=Se activation protocol. The complexes [(Py^NHC)Cu(PPh₃ )₂ ]X, X=BF₄ (1), ClO₄ (2), PF₆ (3) and OTf (4); Py^NHC=3-isopropyl-1-(pyridin-2-yl)-imidazol-2-ylidene, and [(Py^NHC)Cu(PPh₃ )(X)], X=Br (5) and I (6) have been synthesized by treating 1-isopropyl-3-(pyridin-2-yl)-imidazole-2-selone with corresponding copper(I) precursors and triphenylphosphine. In this synthetic strategy, N-heterocyclic carbene gets transferred from N-heterocyclic selone through a C=Se bond cleavage reaction to form copper(I) complexes within five minutes at room temperature. In addition, the mechanism responsible for the C=Se bond cleavage reaction has been fully investigated. These reactions are not sensitive to moisture and oxygen.

Keywords: Bond Cleavage; Carbene; Copper; Organo selenium; Phosphine.

Abstract

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