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Oxygen‐Involved Oxidative Deacetylation of α‐Substituted β‐Acetyl Amides – Synthesis of α‐Keto Amides
Author(s) -
Li Dianjun,
Yu Wei
Publication year - 2013
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201300660
Subject(s) - chemistry , boron trifluoride , yield (engineering) , oxygen , oxidative phosphorylation , medicinal chemistry , oxidative cleavage , acetylation , bond cleavage , chloride , cleavage (geology) , organic chemistry , boron , catalysis , biochemistry , materials science , geotechnical engineering , fracture (geology) , engineering , metallurgy , gene
α‐Substituted β‐acetyl amides could undergo CC bond cleavage to form α‐keto amides when treated with copper(II) chloride (CuCl 2 ) and boron trifluoride diethyl etherate (BF 3 ⋅OEt 2 ) under an oxygen atmosphere. The yield can be increased by the addition of tert ‐butyl hydroperoxide which alone can also effect the reaction. The reaction provides a new protocol for the synthesis of α‐keto amides.