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.
Strotman
Neil A
NA
Department of Process Chemistry, Merck Research Laboratories, Merck & Co., Inc., P.O. Box 2000, Rahway, New Jersey 07065, USA. neil_strotman@merck.com
Chobanian
Harry R
HR
He
Jiafang
J
Guo
Yan
Y
Dormer
Peter G
PG
Jones
Christina M
CM
Steves
Janelle E
JE
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