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. 2013 Jan 7;52(2):615-9.
doi: 10.1002/anie.201207750. Epub 2012 Nov 22.

Mild and general conditions for negishi cross-coupling enabled by the use of palladacycle precatalysts

Yang Yang  1 , Nathan J Oldenhuis, Stephen L Buchwald
Affiliations

Mild and general conditions for negishi cross-coupling enabled by the use of palladacycle precatalysts

Yang Yang et al. Angew Chem Int Ed Engl. .

Abstract

A wide range of biaryls were synthesized by palladium-catalyzed Negishi cross-couplings at ambient temperature or with low catalyst loading. This protocol features the use of a recently reported aminobiphenyl palladacycle precatalyst to generate the catalytically active XPhosPd(0) species. Significantly, a wide range of challenging heterocyclic and polyfluorinated aromatic substrates can be employed to give products in excellent yields.

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Figures

Figure 1
Figure 1
Comparison of precatalyst 3c with several other palladium sources. Conditions: p-tolylzinc chloride (0.65 mmol), 2-bromoanisole (0.5 mmol), Pd (0.1%, Pd:L = 1:1), L = L3, THF, 75 °C, 20 min; yields were determined by GC analysis of the crude reaction mixture.
Figure 2
Figure 2
Comparison of precatalysts with different dialkylbiarylphosphine ligands. Conditions: p-tolylzinc chloride (0.65 mmol), 2-bromoanisole (0.5 mmol), 3 (0.1%), L = L2-5 (0.1%), THF, 75 °C.
Scheme 1
Scheme 1
Precatalysts and Ligands Employed for Negishi Cross-Coupling Reactions.
See this image and copyright information in PMC

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