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Electricity Driven 1,3‐Oxohydroxylation of Donor‐Acceptor Cyclopropanes: a Mild and Straightforward Access to β‐Hydroxy Ketones
Author(s) -
Saha Debarshi,
Maajid Taily Irshad,
Banerjee Prabal
Publication year - 2021
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.202101022
Subject(s) - chemistry , cyclopropane , cyclic voltammetry , acceptor , aryl , electrochemistry , ring (chemistry) , electron acceptor , electron donor , stereochemistry , photochemistry , medicinal chemistry , combinatorial chemistry , organic chemistry , catalysis , physics , alkyl , electrode , condensed matter physics
An unprecedented external oxidant‐free electrochemical protocol for 1, 3‐oxohydroxylation of donor‐acceptor cyclopropane is disclosed. The strategy encompasses the activation of the labile π‐electron cloud of the aryl ring to cleave the strained C sp 3 −C sp 3 bond of cyclopropane to afford the β ‐hydroxy ketones via insertion of molecular oxygen. More significantly, based on the detailed mechanistic investigations and cyclic voltammetry experiments, a plausible mechanism is proposed.