Catalyst-controlled regioselective Suzuki couplings at both positions of dihaloimidazoles, dihalooxazoles, and dihalothiazoles.
Various dihaloazoles can be monoarylated at a single C-X bond with high selectivity via Suzuki coupling. By changing the palladium catalyst employed, the selectivity can be switched for some dihaloazoles, allowing for Suzuki coupling at the other, traditionally less reactive C-X bond. These conditions are applicable to coupling of a wide variety of aryl-, heteroaryl-, cyclopropyl-, and vinylboronic acids with high selectivities and enable the rapid construction of diverse arrays of diarylazoles in a modular fashion.
Department of Process Chemistry, Merck Research Laboratories, Merck & Co., Inc., P.O. Box 2000, Rahway, New Jersey 07065, USA. neil_strotman@merck.com
Neil A
NA
Strotman
Harry R
HR
Chobanian
Jiafang
J
He
Yan
Y
Guo
Peter G
PG
Dormer
Christina M
CM
Jones
Janelle E
JE
Steves
D002384:Catalysis; D003432:Cross-Linking Reagents / Q000737:chemistry; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D010080:Oxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D010165:Palladium; D013237:Stereoisomerism; D013844:Thiazoles / Q000138:chemical synthesis* / Q000737:chemistry
D003432:Cross-Linking Reagents; D006846:Hydrocarbons, Halogenated; D007093:Imidazoles; D010080:Oxazoles; D013844:Thiazoles; D010165:Palladium