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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
2-Chloroacetamide, ≥98%
Sigma-Aldrich
Palladium, nanopowder, <25 nm particle size (TEM), ≥99.5%
Sigma-Aldrich
XPhos Pd G2, 98%
Sigma-Aldrich
Palladium, evaporation slug, diam. × L 0.6 cm × 0.6 cm, 99.95% trace metals basis
Sigma-Aldrich
Palladium, powder or granules, 99.99% trace metals basis
Sigma-Aldrich
Palladium, powder, <75 μm, 99.9% trace metals basis
Sigma-Aldrich
Palladium, wire, diam. 0.5 mm, 99.9% trace metals basis
Sigma-Aldrich
Palladium, foil, thickness 1.0 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, foil, thickness 0.025 mm, 99.9% trace metals basis
Sigma-Aldrich
Palladium, wire, diam. 1.0 mm, 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, 99.995% trace metals basis