Publication Details:
Title: Synthesis of Biaryls and Oligoarenes Using Aryl [2-(hydroxymethyl) phenyl] dimethylsilanes
| Author(s) | Jinshui Chen, Masaaki Tanaka, Akhila K Sahoo, Masahide Takeda, Akira Yada, Yoshiaki Nakao, Tamejiro Hiyama : Bulletin of the Chemical Society of Japan, 2010, 83 (5), 554-569 |
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| Journal Name | Bulletin of the Chemical Society of Japan |
| journal image URL | http://chemistry.uohyd.ac.in/~aks/wp-content/uploads/bulletinofjapan_logo.png |
More Details:
Through intramolecular activation, highly stable aryl[2-(hydroxymethyl)phenyl]dimethylsilanes can selectively transfer their aryl groups to effect a cross-coupling reaction with various aryl bromides and chlorides in the presence of a weak non-fluoride base and a palladium/copper catalyst. This reaction tolerates a wide range of functional groups, producing the corresponding functionalized biaryls in high yields with excellent chemoselectivity. Newly disclosed reaction conditions allow the recovery of a cyclic silyl ether in modest-to-good yields and reuse for the synthesis of the arylsilanes. The introduction of two isopropyl groups on the silicon center instead of methyl groups improves the stability and allows quantitative recovery of the silicon residue. Finally, aryl halides having an O-protected [2-(hydroxymethyl)phenyl]dimethylsilyl group cross-couple with the arylsilane reagents to give silyl-functionalized biaryls.