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Palladium-catalyzed α-arylation of 2-chloroacetates and 2-chloroacetamides.

Palladium-catalyzed α-arylation of 2-chloroacetates and 2-chloroacetamides.

The Journal of organic chemistry (2013-04-11)

Gary A Molander, Kaitlin M Traister, Thiago Barcellos

ABSTRACT

A method has been developed for the Pd-catalyzed synthesis of α-(hetero)aryl esters and amides through a Suzuki-Miyaura cross-coupling reaction. This method avoids the use of strong base, does not necessitate inert or low temperature formation of reagents, and does not require the use of a large excess of organometallic reagent. Utilization of organotrifluoroborate salts as nucleophilic partners allows a variety of functional groups and heterocyclic compounds to be tolerated.

MATERIALS

Product Number

Brand

Product Description

Sigma-Aldrich

2-Chloroacetamide, ≥98.0% (HPLC)

Sigma-Aldrich

Palladium black, 99.95% trace metals basis

Sigma-Aldrich

2-Chloroacetamide, ≥98%

Sigma-Aldrich

Palladium, nanopowder, <25 nm particle size (TEM), ≥99.5%

Sigma-Aldrich

Palladium, evaporation slug, diam. × L 0.9 cm × 1.2 cm, 99.95% trace metals basis

Sigma-Aldrich

Potassium 1-(phenylsulfonyl)-1H-indole-3-trifluoroborate, 95%

Sigma-Aldrich

Palladium, evaporation slug, diam. × L 0.6 cm × 0.6 cm, 99.95% trace metals basis

Sigma-Aldrich

Palladium, wire, diam. 0.5 mm, 99.9% trace metals basis

Sigma-Aldrich

Palladium, foil, thickness 0.25 mm, 99.98% trace metals basis

Sigma-Aldrich

Palladium, sponge, 99.9% trace metals basis

Sigma-Aldrich

Palladium, powder, <1 μm, ≥99.9% trace metals basis

Sigma-Aldrich

Palladium, foil, thickness 0.5 mm, 99.9% trace metals basis

Sigma-Aldrich

Palladium, powder or granules, 99.99% trace metals basis

Sigma-Aldrich

Palladium, foil, thickness 0.05 mm, 99.9% trace metals basis

Sigma-Aldrich

Palladium, powder, <75 μm, 99.9% trace metals basis

Sigma-Aldrich

Palladium, powder, 99.995% trace metals basis

Sigma-Aldrich

Palladium, extent of labeling: 5 wt. % loading (dry basis), matrix activated carbon, wet support, Degussa type E105CA/W

Sigma-Aldrich

Palladium, wire, diam. 1.0 mm, 99.9% trace metals basis

Sigma-Aldrich

XPhos Pd G2, 98%

Sigma-Aldrich

Palladium, foil, thickness 0.025 mm, 99.9% trace metals basis

Sigma-Aldrich

Palladium, foil, thickness 1.0 mm, 99.9% trace metals basis