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Synthesis of Carbamates by Direct C–H Bond Activation of Formamides
Author(s) -
Barve Balaji D.,
Wu YangChang,
ElShazly Mohamed,
Chuang DaWei,
Chung YuMing,
Tsai YiHong,
Wu ShouFang,
Korinek Michal,
Du YingChi,
Hsieh ChiTing,
Wang JehJeng,
Chang FangRong
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.201201160
Subject(s) - formamides , chemistry , stereoselectivity , derivative (finance) , phenols , reaction conditions , organic chemistry , medicinal chemistry , combinatorial chemistry , catalysis , financial economics , economics
Copper catalysed oxidative coupling reaction of formamides with β‐keto esters and 2‐carbonyl‐substituted phenols successfully proceeded through direct C–H bond activation of formamides. The corresponding carbamates were formed with high stereoselectivity under mild reaction conditions. This protocol was successfully applied to the synthesis of three novel halogenated carbamates and a carbaryl insecticide derivative. Our results suggest the use of 6.0 equiv. TBHP is crucial for this type of reaction.