Ring size and nothing else matters: unusual regioselectivity of alkyne hydration by NHC gold(<scp>i</scp>) complexes
Sergey A. Rzhevskiy, Anna N. Philippova, Gleb A. Chesnokov, Alexandra A. Ageshina, Lidiya I. Minaeva, Maxim A. Topchiy, M.S. Nechaev, Andrey F. Asachenko
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.
Topics & Concepts
RegioselectivitySteric effectsAlkyneChemistryRing (chemistry)Markovnikov's ruleRing sizeStereochemistryOrganic chemistryCatalysisCatalytic Alkyne ReactionsCatalytic Cross-Coupling ReactionsN-Heterocyclic Carbenes in Organic and Inorganic Chemistry