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(Diacetoxyiodo)benzene‐mediated Selective Synthesis of α‐Azido Ketones or Acyl Azides from β‐Keto Acids
Author(s) -
Zheng ZhaoJing,
Yu TianYang,
Xu PengFei,
Wei Hao
Publication year - 2018
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.201800319
Subject(s) - chemistry , ketone , azide , benzene , reagent , selectivity , organic chemistry , combinatorial chemistry , catalysis
(Diacetoxyiodo)benzene‐mediated selective synthesis of α‐azido ketones or acyl azides from keto acids is developed. The selectivity depends on the amounts of the reagents used. Treatment of β‐keto acid derivatives with 1.2 or 2.2 equivalents of (diacetoxyiodo)benzene results in α‐azido ketone or acyl azide products, respectively. Initial mechanistic studies show that monobromomethyl ketone and dibromomethyl ketone are plausible intermediates in these reactions.