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Reduction of Activated Carbonyl Groups Using Alkylphosphanes as Reducing Agents: A Mechanistic Study
Author(s) -
Wei Yin,
Liu XuGuang,
Shi Min
Publication year - 2012
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.201200019
Subject(s) - chemistry , reduction (mathematics) , cleavage (geology) , carbonyl group , combinatorial chemistry , proton , computational chemistry , stereochemistry , geometry , mathematics , geotechnical engineering , fracture (geology) , engineering , physics , quantum mechanics
Abstract A comprehensive mechanistic investigation on the reduction of activated carbonyl groups using alkylphosphanes as reducing agents has been conducted through a combination of experimental as well as computational studies. Both approaches show that this kind of reduction proceeds either through proton transfer from alkylphosphanes and cleavage by water during work‐up or through another reaction pathway involving the participation of water at the initial stage and a two‐fold proton transfer to afford the product.