Ring size and nothing else matters: unusual regioselectivity of alkyne hydration by NHC gold(I) complexes

Sergey A Rzhevskiy; Anna N Philippova; Gleb A Chesnokov; Alexandra A Ageshina; Lidiya I Minaeva; Maxim A Topchiy; Mikhail S Nechaev; Andrey F Asachenko

doi:10.1039/d1cc01837j

Ring size and nothing else matters: unusual regioselectivity of alkyne hydration by NHC gold(I) complexes

Chem Commun (Camb). 2021 Jun 8;57(46):5686-5689. doi: 10.1039/d1cc01837j.

Authors

Sergey A Rzhevskiy¹, Anna N Philippova¹, Gleb A Chesnokov¹, Alexandra A Ageshina¹, Lidiya I Minaeva¹, Maxim A Topchiy¹, Mikhail S Nechaev², Andrey F Asachenko¹

Affiliations

¹ A.V. Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences, Leninsky Prospect 29, Moscow, 119991, Russian Federation. aasachenko@ips.ac.ru.
² A.V. Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences, Leninsky Prospect 29, Moscow, 119991, Russian Federation. aasachenko@ips.ac.ru and M.V. Lomonosov Moscow State University, Leninskie Gory 1 (3), Moscow, 119991, Russian Federation.

PMID: 33978647
DOI: 10.1039/d1cc01837j

Abstract

We have investigated the role of ring sizes and substituents in NHC ligands in some (NHC)Au(i) complexes in the hydration of internal alkynes. Despite the fact that using (NHC)Au(i) complexes in the hydration of diarylacetylenes leads to Markovnikov-type products, the precise tuning of ligands allows changing the regioselectivity in arylalkylacetylene hydration to the anti-Markovnikov-type.