Graphene-Catalyzed Direct Friedel-Crafts Alkylation Reactions: Mechanism, Selectivity, and Synthetic Utility.
Transition-metal-catalyzed alkylation reactions of arenes have become a central transformation in organic synthesis. Herein, we report the first general strategy for alkylation of arenes with styrenes and alcohols catalyzed by carbon-based materials, exploiting the unique property of graphenes to produce valuable diarylalkane products in high yields and excellent regioselectivity. The protocol is characterized by a wide substrate scope and excellent functional group tolerance. Notably, this process constitutes the first general application of graphenes to promote direct C-C bond formation utilizing polar functional groups anchored on the GO surface, thus opening the door for an array of functional group alkylations using benign and readily available graphene materials. Mechanistic studies suggest that the reaction proceeds via a tandem catalysis mechanism in which both of the coupling partners are activated by interaction with the GO surface.
Department of Chemistry, Rutgers University , 73 Warren Street, Newark, New Jersey 07102, United States.
Feng
F
Hu
Department of Chemistry, Rutgers University , 73 Warren Street, Newark, New Jersey 07102, United States.
Mehulkumar
M
Patel
Department of Chemistry and Chemical Biology, Rutgers University , 610 Taylor Rd, Piscataway, New Jersey 08854, United States.
Feixiang
F
Luo
Department of Chemistry, Rutgers University , 73 Warren Street, Newark, New Jersey 07102, United States.
Carol
C
Flach
Department of Chemistry, Rutgers University , 73 Warren Street, Newark, New Jersey 07102, United States.
Richard
R
Mendelsohn
Department of Chemistry and Chemical Biology, Rutgers University , 610 Taylor Rd, Piscataway, New Jersey 08854, United States.
Eric
E
Garfunkel
Department of Chemistry, Rutgers University , 73 Warren Street, Newark, New Jersey 07102, United States.
Huixin
H
He
Department of Chemistry, Rutgers University , 73 Warren Street, Newark, New Jersey 07102, United States.
Michal
M
Szostak