Facile and highly selective conversion of nitriles to amides via indirect acid-catalyzed hydration using TFA or AcOH-H2SO4

Facile and highly selective conversion of nitriles to amides via indirect acid-catalyzed hydration using TFA or AcOH-H2SO4
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DOI:
10.1021/jo048240a
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发表时间:
2005-03-04
影响因子:
3.6
通讯作者:
Singhal, N
Singhal, N
中科院分区:
化学2区
文献类型:
--
作者:
Moorthy, JN;Singhal, N

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以TFA-H2SO4混合物为试剂体系,通过间接酸催化水化反应,在1-8 h内,脂肪族和芳香族腈均可方便、选择性地一步转化为相应的酰胺。虽然相同的试剂对位阻腈(如甲腈)不起作用,但可以通过在更高的温度(bb0 - 90℃)下将TFA转化为AcOH来完成。
Both aliphatic and aromatic nitriles are conveniently and selectively converted in a single step, via an indirect acid-catalyzed hydration, into the corresponding amides in 1-8 h using a TFA-H2SO4 mixture as a reagent system. Although the same reagent did not work for the sterically hindered nitriles such as mesitonitrile, the transformation could be accomplished by changing TFA to AcOH at higher temperatures (>90 degreesC).