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Highly Regioselective Hydroaminomethylation of Terminal Olefins to Linear Amines Using Rh Complexes with a Tetrabi Phosphorus Ligand
Author(s) -
Liu Guodu,
Huang Kexuan,
Cai Chaoxian,
Cao Bonan,
Chang Mingxin,
Wu Wenjun,
Zhang Xumu
Publication year - 2011
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201103073
Subject(s) - regioselectivity , chemoselectivity , chemistry , amine gas treating , ligand (biochemistry) , yield (engineering) , medicinal chemistry , rhodium , selectivity , substrate (aquarium) , hydroamination , organic chemistry , catalysis , materials science , receptor , biochemistry , oceanography , metallurgy , geology
A highly regioselective hydroaminomethylation of terminal olefins catalyzed by Rh complexes with 2, 2′, 6, 6′‐tetrakis ((diphenylphosphino)methyl)‐1, 1′‐biphenyl (Tetrabi) ligand has been developed. Up to 99 % amine selectivity, 168 linear/branched amine product ratio ( n/i ), and 97.4 % linear amine yield has been obtained at a substrate/rhodium precursor ratio (S/Rh) of 1000 with this methodology. The turnover number was achieved 6930 at 10000 S/Rh ratio, and the n/i can reach up to >525. Several different olefins and secondary amines have been applied successfully with high chemoselectivity (99 %), yield (>98 %), and regioselectivity (>120).