Nickel-Catalyzed Suzuki–Miyaura Couplings in Green Solvents

Nickel-Catalyzed Suzuki–Miyaura Couplings in Green Solvents

Stephen D. Ramgren, Liana Hie, Yuxuan Ye, and Neil K. Garg

Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, California 90095-1569, United States

Org. Lett., Article ASAP

Publication Date (Web): July 23, 2013 (Letter)

DOI: 10.1021/ol401727y

http://pubs.acs.org/doi/abs/10.1021/ol401727y

The nickel-catalyzed Suzuki–Miyaura coupling of aryl halides and phenol-derived substrates with aryl boronic acids using green solvents, such as 2-Me-THF and tert-amyl alcohol, is reported. This methodology employs the commercially available and air-stable precatalyst, NiCl2(PCy3)2, and gives biaryl products in synthetically useful to excellent yields. Using this protocol, bis(heterocyclic) frameworks can be assembled efficiently.