Issue 3, 2022

The structures of ring-expanded NHC supported copper(i) triphenylstannyls and their phenyl transfer reactivity towards heterocumulenes

Abstract

Three ring-expanded N-heterocyclic carbene-supported copper(I) triphenylstannyls have been synthesised by the reaction of (RE-NHC)CuOtBu with triphenylstannane (RE-NHC = 6-Mes, 6-Dipp, 7-Dipp). The compounds were characterised by NMR spectroscopy and X-ray crystallography. Reaction of (6-Mes)CuSnPh3 with di-p-tolyl carbodiimide, phenyl isocyanate and phenylisothiocyanate gives access to a copper(I) benzamidinate, benzamide and benzothiamide respectively via phenyl transfer from the triphenylstannyl anion with concomitant formation of (Ph2Sn)n. Attempts to exploit this reactivity under a catalytic regime were hindered by rapid copper(I)-catalysed dismutation of Ph3SnH to Ph4Sn, various perphenylated tin oligomers, H2 and a metallic material thought to be Sn(0). Mechanistic insight was provided by reaction monitoring via NMR spectroscopy and mass spectrometry.

Graphical abstract: The structures of ring-expanded NHC supported copper(i) triphenylstannyls and their phenyl transfer reactivity towards heterocumulenes

Supplementary files

Article information

Article type
Communication
Submitted
14 Sept. 2021
Accepted
22 Dec. 2021
First published
22 Dec. 2021
This article is Open Access
Creative Commons BY-NC license

Dalton Trans., 2022,51, 831-835

The structures of ring-expanded NHC supported copper(I) triphenylstannyls and their phenyl transfer reactivity towards heterocumulenes

R. S. C. Charman, M. F. Mahon, J. P. Lowe and D. J. Liptrot, Dalton Trans., 2022, 51, 831 DOI: 10.1039/D1DT03109K

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