Open Access“Benchtop” Biaryl Coupling Using Pd/Cu Cocatalysis: Application to the Synthesis of Conjugated Polymers
Author(s) -
Matthew B. Minus,
Sarah R. Moor,
Fathima F. Pary,
L. P. Tharika Nirmani,
Malgorzata Chwatko,
Brandon Okeke,
Josh E. Singleton,
Toby L. Nelson,
Nathaniel A. Lynd,
Eric V. Anslyn
Publication year - 2021
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.1c00479
Subject(s) - polyfluorene , aryl , chemistry , conjugated system , bimetallic strip , polymer , inert , palladium , suzuki reaction , context (archaeology) , inert gas , combinatorial chemistry , copper , nanotechnology , polymer chemistry , chemical engineering , organic chemistry , catalysis , materials science , paleontology , alkyl , engineering , biology
Typically, Suzuki couplings used in polymerizations are performed at raised temperatures in inert atmospheres. As a result, the synthesis of aromatic materials that utilize this chemistry often demands expensive and specialized equipment on an industrial scale. Herein, we describe a bimetallic methodology that exploits the distinct reactivities of palladium and copper to perform high yielding aryl-aryl dimerizations and polymerizations that can be performed on a benchtop under ambient conditions. These couplings are facile and can be performed by simple mixing in the open vessel. To demonstrate the utility of this method in the context of polymer synthesis: polyfluorene, polycarbazole, polysilafluorene, and poly(6,12-dihydro-dithienoindacenodithiophene) were created at ambient temperature and open to air.