Premium
Metal‐free Intermolecular Hydrophenoxylation of Aryl Alkynes
Author(s) -
Patel Monika,
Saunthwal Rakesh K.,
Dhaked Devendra K.,
Bharatam Prasad V.,
Verma Akhilesh K.
Publication year - 2016
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201500479
Subject(s) - chemistry , superbase , nucleophile , aryl , markovnikov's rule , regioselectivity , stereoselectivity , nucleophilic addition , phenols , intermolecular force , organic chemistry , combinatorial chemistry , computational chemistry , molecule , catalysis , alkyl
Base‐mediated anti‐Markovnikov additions of phenols onto terminal alkynes have been achieved. This paper presents insights into the role of DMSO in superbase‐mediated chemo‐, regio‐, and stereoselective nucleophilic addition reactions of phenols onto aryl alkynes. Deuterium‐labeling experiments uncover that the source of styryl protons in the products comes from the DMSO, not from the substrate (nucleophile) nor from the water workup. Competitive nucleophilic additions and the mechanistic pathway was corroborated by control experiments and computational calculations.