Microwave-assisted heterogeneous cross-coupling reactions catalyzed by nickel-in-charcoal (Ni/C).
A study involving the relatively rare combination of heterogeneous catalysis conducted under microwave conditions is presented. Carbon-carbon bond formation, including Negishi and Suzuki couplings, can be quickly effected with aryl chloride partners by using a base metal (nickel) adsorbed in the pores of activated charcoal. Aminations were also studied, along with cross-couplings of vinyl alanes with benzylic chlorides as a means to stereodefined allylated aromatics. Reaction times for all these processes are typically reduced from several hours to minutes in a microwave reactor.
Lipshutz
Bruce H
BH
Department of Chemistry and Biochemistry, University of California, Santa Barbara, CA 93106, USA. lipshutz@chem.ucsb.edu
Frieman
Bryan A
BA
Lee
Ching-Tien
CT
Lower
Asher
A
Nihan
Danielle M
DM
Taft
Benjamin R
BR
D002244:Carbon / Q000737:chemistry; D002384:Catalysis; D002606:Charcoal / Q000737:chemistry*; D002626:Chemistry, Pharmaceutical / Q000295:instrumentation / Q000379:methods*; D002712:Chlorides / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008670:Metals / Q000737:chemistry; D008872:Microwaves; D008956:Models, Chemical; D009532:Nickel / Q000737:chemistry*; D017550:Spectroscopy, Fourier Transform Infrared; D013678:Technology, Pharmaceutical / Q000295:instrumentation / Q000379:methods*; D013696:Temperature; D014465:Ultrasonics
D002712:Chlorides; D008670:Metals; D002606:Charcoal; D002244:Carbon; D009532:Nickel