Catalyst-Controlled Chemoselective Arylation of 2-Aminobenzimidazoles-

Reaction Scheme

Abstract

Pd2(dba)3/tris(tert-butyl)�HBF4/KF�2H2O serves as a mild, robust, and user-friendly method for the efficient Suzuki cross-coupling of a diverse array of aryl and heteroaryl halides with aryl- and heteroarylboronic acids.

Substrates

Procedure

Pd2(dba)3/[ (t-Bu)3]BF4 [Pd: (t-Bu)3 = 1:1.2 ; 8.1 mg, 0.0050 mmol of Pd2 (dba)3], the boronic acid (1.10 mmol), and KF�2 H2O (310 mg, 3.30 mmol) were added to a 4-mL vial that contained a stir bar. The vial was purged with argon for 3 min, and then it was sealed with a septum cap. THF (2.0 mL) and the aryl halide (1.00 mmol) were added, and the reaction mixture was stirred at room temperature. Next, the mixture was diluted with Et2O (2 mL) and filtered through a plug of silica gel [washed with Et2O (10mL)]. The filtrate was concentrated, and the residue was purified by flash chromatography on silica gel.

Products

Materials

     
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