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Bismuth‐Catalyzed Direct Substitution of the Hydroxy Group in Alcohols with Sulfonamides, Carbamates, and Carboxamides
Author(s) -
Qin Hongbo,
Yamagiwa Noriyuki,
Matsunaga Shigeki,
Shibasaki Masakatsu
Publication year - 2007
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200602909
Subject(s) - allylic rearrangement , chemistry , bismuth , yield (engineering) , amine gas treating , catalysis , substitution (logic) , alcohol , substitution reaction , organic chemistry , combinatorial chemistry , materials science , computer science , metallurgy , programming language
No preactivation of the alcohol substrates is required in allylic, propargylic, and benzylic aminations catalyzed by a combination of commercially available Bi(OTf) 3 and KPF 6 , mostly at room temperature (see scheme). The substitution reactions of readily accessible allylic, propargylic, and benzylic alcohols with sulfonamides, carbamates, and carboxamides give the desired amine products in up to 99 % yield.