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Photoredox Catalysis of Intramolecular Cyclizations with a Reusable Silica‐Bound Ruthenium Complex
Author(s) -
Barbante Gregory J.,
Ashton Trent D.,
Doeven Egan H.,
Pfeffer Frederick M.,
Wilson David J. D.,
Henderson Luke C.,
Francis Paul S.
Publication year - 2015
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201500304
Subject(s) - ruthenium , catalysis , photoredox catalysis , intramolecular force , chemistry , chromophore , amine gas treating , carbodiimide , combinatorial chemistry , organic chemistry , photocatalysis , photochemistry
Photoredox catalysis with the use of a stable, reusable silica‐bound chromophore was applied to the intramolecular cyclization of a series of 2‐benzylidenehydrazinecarbothioamides to give 5‐phenyl‐1,3,4‐thiadiazol‐2‐amines. The catalyst was readily prepared by carbodiimide‐mediated coupling of commercially available amine‐functionalized silica beads to a carboxylic acid functionalized ruthenium complex. The immobilized catalyst was readily removed from the reaction product by filtration and was used eight times without loss of catalytic activity. This simple, safe, and practical method is an attractive alternative to conventional procedures.