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Selenium‐Catalyzed Reductive Carbonylation of 2‐Nitrophenols to2‐Benzoxazolones
Author(s) -
Wang Xiaofang,
Ling Gang,
Xue Yan,
Lu Shiwei
Publication year - 2005
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.200400561
Subject(s) - chemistry , atmospheric pressure , catalysis , carbonylation , selenium , base (topology) , solvent , inorganic chemistry , phase (matter) , nitro compound , organic chemistry , nitro , carbon monoxide , mathematical analysis , oceanography , mathematics , geology , alkyl
2‐Benzoxazolones or 2‐benzimidazolones are synthesized in moderate to good yields in the presence of a base (KOH, NaOH, KOAc, NEt 3 , DBU) at atmospheric pressure or under a high pressure of CO by one‐pot reductive carbonylation of 2‐nitrophenols or 2‐nitroaniline in the presence of selenium as catalyst. Besides the effect of base, the effects of solvent and temperature on the reaction were investigated at high or atmospheric pressure. Contrasting results were obtained for 2‐benzoxazolones or 2‐benzimidazolone at high and atmospheric pressures. Moreover, phase‐transfer catalysis was exhibited. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)