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. 2013 Aug 2;15(15):3950-3.
doi: 10.1021/ol401727y. Epub 2013 Jul 23.

Nickel-catalyzed Suzuki-Miyaura couplings in green solvents

Stephen D Ramgren  1 , Liana Hie, Yuxuan Ye, Neil K Garg
Affiliations

Nickel-catalyzed Suzuki-Miyaura couplings in green solvents

Stephen D Ramgren et al. Org Lett. .

Abstract

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.

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Figures

Figure 1
Figure 1
Suzuki–Miyaura cross-coupling of aryl halides and phenol derivatives in green solvents.
Figure 2
Figure 2
Coupling of heterocyclic halides with aryl boronic acids.a,b
Figure 3
Figure 3
Coupling of heterocyclic phenolic derivatives with aryl boronic acids.a,b
Figure 4
Figure 4
Coupling of heterocyclic substrates with heterocyclic aryl boronic acids.a,b
Figure 5
Figure 5
Gram scale couplings.a,b
See this image and copyright information in PMC

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