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A General Study of Aryloxo and Alkoxo Ligands in the Titanium‐Catalyzed Intermolecular Hydroamination of Terminal Alkynes
Author(s) -
Tillack Annegret,
Khedkar Vivek,
Jiao Haijun,
Beller Matthias
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.200500423
Subject(s) - markovnikov's rule , hydroamination , regioselectivity , chemistry , catalysis , intermolecular force , ligand (biochemistry) , titanium , stereochemistry , medicinal chemistry , organic chemistry , molecule , receptor , biochemistry
A general study of the regioselective hydroamination of terminal alkynes in the presence of Ti(NEt 2 ) 4 and different aryloxo and alkoxo ligands is presented. Depending on the ligand the regioselectivity towards the Markovnikov and the anti ‐Markovnikov addition product can be controlled. The experimentally observed isomer distribution is explained perfectly by detailed theoretical investigations which demonstrate that the regioselectivity is determined by the relative stability of the corresponding alkynetitanium π complexes. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)