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Green Regio‐ and Enantioselective Aminolysis Catalyzed by Graphite and Graphene Oxide under Solvent‐Free Conditions
Author(s) -
Acocella Maria Rosaria,
D'Urso Luciana,
Maggio Mario,
Guerra Gaetano
Publication year - 2016
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.201600241
Subject(s) - aminolysis , epoxide , graphene , catalysis , oxide , styrene oxide , enantioselective synthesis , chemistry , graphite oxide , organic chemistry , nucleophile , aryl , enantiomeric excess , styrene , materials science , nanotechnology , copolymer , polymer , alkyl
The ring‐opening reactions of epoxides with amines were efficiently and regioselectively catalyzed by high‐surface‐area graphite and graphene oxide under metal‐free and solvent‐free conditions. For epoxides without aryl groups, catalytic activity was observed only for graphene oxide, and hence, the activity must have been due to its acidic groups. For styrene oxide, instead, graphite and graphene oxide exhibited rather similar catalytic activities, and hence, the activity was mainly due to activation of the electrophilic epoxide by π‐stacking interactions with the graphitic π system. The described aminolysis procedure is green and cheap because the catalyst can be recovered and recycled without loss of efficiency. Moreover, these heterogeneous catalysts exert high stereoselective control in the presence of nonracemic epoxides and provide chiral β‐amino alcohols with enantiomeric excess values up to 99 %.