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DOI: 10.1055/s-2008-1042932
Palladium-Catalyzed Addition of Arylboronic Acids to N-Tosylarylimines
Publication History
Publication Date:
11 March 2008 (online)
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Abstract
Pd-catalyzed addition of arylboronic acids to N-tosylarylimines was described by employing easily prepared, air-stable aminophosphine ligands, cheap inorganic base, and common organic solvents, providing diarylmethylamine derivatives through one-pot synthesis in moderate to good yields. The efficiency of this reaction was demonstrated by the compatibility with nitro, trifluoromethyl, fluoro, chloro, and methoxy groups. Moreover, rigorous exclusion of air/moisture is not required in these transformations.
Key words
N-tosylarylimines - arylboronic acids - palladium-catalyzed - aminophosphine ligands - diarylmethylamine derivatives
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References and Notes
General Procedures
A Schlenk reaction tube was charged with PdCl2(PhCN)2 (9.6 mg, 0.05 mmol), i-Pr2NPPh2 (7.2 mg, 0.05 mmol), arylboronic acids (1.0 mmol), N-tosylarylimines (0.5 mmol), K2CO3 (207 mg, 1.5 mmol), 4 Å MS (100 mg), and anhydrous dioxane (3 mL). The reaction tube was purged with N2 under salted ice (ca. -10 °C). The mixture was stirred for 0.5 h at r.t. Then, the mixture was heated at 80 °C for the given time. After completion of the reaction, as indicated by TLC, the reaction mixture was concentrated in vacuo and the residue was purified by flash column chromatography on a silica gel to give the product.