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General Zinc‐Catalyzed Intermolecular Hydroamination of Terminal Alkynes
Author(s) -
Alex Karolin,
Tillack Annegret,
Schwarz Nicolle,
Beller Matthias
Publication year - 2008
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.200700160
Subject(s) - hydroamination , chemistry , catalysis , markovnikov's rule , amination , zinc , regioselectivity , trifluoromethanesulfonate , homogeneous catalysis , atom economy , intermolecular force , combinatorial chemistry , yield (engineering) , organic chemistry , medicinal chemistry , molecule , materials science , metallurgy
Catalytic hydroaminations are one of the most sustainable CN bond‐forming processes as a result of 100 % atom economy and the availability of substrates. Here, it is shown that the intermolecular hydroamination of terminal alkynes with anilines proceeds smoothly in the presence of catalytic amounts of zinc triflate, an easily available and inexpensive zinc salt. Amination and subsequent reduction with NaBH 3 CN gives a variety of secondary and tertiary amines in up to 99 % yield and with over 99 % Markovnikov regioselectivity. Moreover, difficult functional groups such as nitro and cyano substituents are tolerated by the homogeneous catalyst.