Ring size and nothing else matters: unusual regioselectivity of alkyne hydration by NHC gold(i) complexes. Issue 46 (12th May 2021)

• Record Type: Journal Article
• Authors: Rzhevskiy, Sergey A.; Philippova, Anna N.; Chesnokov, Gleb A.; Ageshina, Alexandra A.; Minaeva, Lidiya I.; Topchiy, Maxim A.; Nechaev, Mikhail S.; Asachenko, Andrey F.
• Is Part Of: Chemical communications. Volume 57:Issue 46(2021)
• Page Start: 5686
• Page End: 5689
• Publication Date: 2021-05-12
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/d1cc01837j
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : We have found that expanded-ring NHC gold(i ) complexes efficiently and regioselectively catalyze the hydration of alkylarylacetylenes in an anti-Markovnikov fashion due to steric repulsion build-up in the transition state, giving benzylalkyl ketones. 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.