Direct Arylation of Aryl(azaaryl)methanes

T. Niwa; H. Yorimitsu; K. Oshima

doi:10.1055/s-2007-968894

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Synfacts 2007(9): 0930-0930
DOI: 10.1055/s-2007-968894

Synthesis of Materials and Unnatural Products

Direct Arylation of Aryl(azaaryl)methanes

Contributor(s): Timothy M. Swager, Koushik Venkatesan
T. Niwa, H. Yorimitsu*, K. Oshima*
Kyoto University, Japan

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Publikationsdatum:
23. August 2007 (online)

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Significance

The authors report a new repertoire of direct arylation of sp³ C-H bonds and direct arylation of diarylmethanes providing triarylmethanes. Treatment of chlorobenzene with 2-benzylpyrimidine in the presence of cesium hydroxide under PdCl₂/tricyclohexylphosphine (PCy₃) catalysis in refluxing xylene provided 2-(diphenylmethyl)pyrimidine in high yield. A variety of aryl chlorides underwent the arylation reaction. Unfortunately, attempted reactions of electron-deficient azaarylmethanes resulted in incomplete conversions.