Palladium-Catalyzed Addition of Arylboronic Acids to N-Tosylarylimines

Qiang Zhang; Jiuxi Chen; Miaochang Liu; Huayue Wu; Jiang Cheng; Changming Qin; Weike Su; Jinchang Ding

doi:10.1055/s-2008-1042932

LETTER

Palladium-Catalyzed Addition of Arylboronic Acids to N-Tosylarylimines

Qiang Zhang^a, Jiuxi Chen^a, Miaochang Liu^a, Huayue Wu*^a, Jiang Cheng*^a, Changming Qin^a, Weike Su^a,b, Jinchang Ding^a
^a College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou, 325027, P. R. of China
Fax: +86(577)88368280; e-Mail: huayuewu@wzu.edu.cn; e-Mail: jiangcheng@wzu.edu.cn;
^b Key Laboratory of Pharmaceutical Engineering, College of Pharmaceutical Sciences, Zhejiang University of Technology, Zhejiang, Hangzhou, 310014, P. R. of China

Abstract

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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

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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.