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Neighboring Carbonyl Group Assisted Hydration of Unsymmetrical Aryl Alkynes Overriding Regular Selectivity
Author(s) -
Mendhekar Kishor L.,
Pradhan Tapas R.,
Mallampudi N. Arjunreddy,
Mohapatra Debendra K.
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900941
Subject(s) - chemistry , regioselectivity , aryl , markovnikov's rule , carbonyl group , functional group , catalysis , stoichiometry , surface modification , group (periodic table) , selectivity , primary (astronomy) , organic chemistry , combinatorial chemistry , medicinal chemistry , alkyl , polymer , physics , astronomy
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.