Mechanism of copper(I)-catalyzed cyclopropanation: a DFT study calibrated with copper(I) alkene complexes

Structural Diversity of Copper(I)–N‐Heterocyclic Carbene Complexes; Ligand Tuning Facilitates Isolation of the First Structurally Characterised Copper(I)–NHC Containing a Copper(I)–Alkene Interaction

“…[1][2][3][4][5] Furthermore, in nature, it is believed that the formation of a copper(I)-ethylene adduct in the ETR 1 plant protein is a key step in the regulation of several aspects of the plant life cycle. [6] As the bonding is relatively weak, many systems take advantage of the reversible binding nature of copper(I)-alkenes.…”

Electronic structure and electrophilic reactivity of discrete copper diphenylcarbenes

“…Several mechanistic [5][6][7][8] and theoretical [8][9][10][11] studies that implicate Cu(I) carbenes [Cu]@CRR 0 as the active species in copper-catalyzed cyclopropanation support these early proposals, though such catalytically active Cu(I) carbenes have proven elusive. A transient copper carbene has been identified via time-resolved FTIR spectroscopy upon addition of N 2 CHCO 2 Me to a cationic bis(oxazoline) Cu(I) precatalyst [12].…”

Copper(I) complexes supported by a heavily fluorinated bis(pyrazolyl)borate: syntheses and characterization of [H2B(3,5-(CF3)2Pz)2]CuL (where L = PPh3, N CCH3, HC CPh, H2C CHPh) and {[H2B(3,5-(CF3)2Pz)2]Cu}2(1,5-COD)

“…Copper(I) olefin complexes are also of interest for a variety of reasons [23,[72][73][74][75][76][77][78]. For example, they serve as models for copper(I) based ethylene receptor sites in plants [79,80] and resting state of the catalyst in copper catalyzed cyclopropanation reactions of olefins [72].…”

“…For example, they serve as models for copper(I) based ethylene receptor sites in plants [79,80] and resting state of the catalyst in copper catalyzed cyclopropanation reactions of olefins [72]. Most alkene (in particular ethylene) complexes of copper are quite labile [23].…”