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Reusable Gold(I) Catalysts with Unique Regioselectivity for Intermolecular Hydroamination of Alkynes
Author(s) -
Leyva Antonio,
Corma Avelino
Publication year - 2009
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200900491
Subject(s) - regioselectivity , hydroamination , chemistry , steric effects , catalysis , phosphine , intermolecular force , combinatorial chemistry , ligand (biochemistry) , tandem , organic chemistry , molecule , biochemistry , materials science , receptor , composite material
Abstract Two gold(I) phosphine complexes bearing the low‐coordinating bis(trifluoromethanesulfonyl)imidate ligand, namely AuSPhosNTf 2 and AuPPh 3 NTf 2 , are active catalysts for the regioselective intermolecular hydroamination of both internal and terminal alkynes under mild reaction conditions. The catalysts show a regioselectivity based on electronic rather than steric factors, which allow the preferential synthesis of regioisomers opposite to those described previously. This subtle chemo‐ and regioselectivity depends on the catalyst, substrates and reaction conditions employed, and allows one to perform new tandem reactions. These gold(I) complexes operate under free‐solvent conditions, without exclusion of air, without addition of acidic promoters and can be quantitatively recovered and reused by simple precipitation in hexane.