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Rhodium(III) Complex with a Bulky Cyclopentadienyl Ligand as a Catalyst for Regioselective Synthesis of Dihydroisoquinolones through C−H Activation of Arylhydroxamic Acids
Author(s) -
Trifonova Evgeniya A.,
Ankudinov Nikita M.,
Kozlov Maxim V.,
Sharipov Mikhail Y.,
Nelyubina Yulia V.,
Perekalin Dmitry S.
Publication year - 2018
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.201804050
Subject(s) - regioselectivity , rhodium , cyclopentadienyl complex , catalysis , ligand (biochemistry) , chemistry , medicinal chemistry , combinatorial chemistry , stereochemistry , organic chemistry , receptor , biochemistry
Catalytic reaction of arylhydroxamic acids with alkenes represents a convenient method for preparation of biologically active dihydroisoquinolones. Here, the rhodium(III) complex [(C 5 H 2 t Bu 2 CH 2 t Bu)RhCl 2 ] 2 , which allows one to carry out such reactions with high regioselectivity to obtain 4‐substituted dihydroisoquinolones in 72–97 % yields, is described. The regioselectivity is provided by the bulky cyclopentadienyl ligand of the catalyst, which is formed through a [2+2+1] cyclotrimerization of tert ‐butylacetylene. The catalytic reaction tolerates various distant functional groups in alkenes, but is inhibited by bulky (e.g., t Bu) or strongly coordinating (e.g., imidazolyl) substituents. Some of the prepared dihydroisoquinolones effectively inhibit growth of phytopathogenic fungi.