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- Title
Neighboring Carbonyl Group Assisted Hydration of Unsymmetrical Aryl Alkynes Overriding Regular Selectivity.
- Authors
Mendhekar, Kishor L.; Pradhan, Tapas R.; Mallampudi, N. Arjunreddy; Mohapatra, Debendra K.
- Abstract
A mild and highly regioselective gold‐catalyzed hydration of γ‐acetoxy aryl alkynes leading to anti‐Markovnikov products by the assistance of a neighboring carbonyl group is presented. The reaction procedure operates under room temperature conditions with broad functional group tolerance in presence of more than stoichiometric amount of water to access two different types of acyloins in good to excellent yields. Acetate protected acyloins were produced from primary and secondary substrates, while tertiary ones react differently to give free‐acyloins under identical conditions. The mechanistic pathways for such divergent functionalization were deduced from isotopic mechanistic results.
- Subjects
CARBONYL group; ALKYNES; ACYLOINS; FUNCTIONAL groups; OPERATING rooms; HYDRATION
- Publication
European Journal of Organic Chemistry, 2019, Vol 2019, Issue 33, p5787
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201900941