The palladium/norbornene-catalyzed ortho-silylmethylation reaction: a practical protocol for ortho-functionalized one-carbon homologation of aryl iodides

Xianwei Sui; Linlin Ding; Zhenhua Gu

doi:10.1039/C6CC08227K

The palladium/norbornene-catalyzed ortho-silylmethylation reaction: a practical protocol for ortho-functionalized one-carbon homologation of aryl iodides

Xianwei Sui,^a Linlin Ding^a and Zhenhua Gu*^a

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* Corresponding authors

^a Department of Chemistry, University of Science and Technology of China, 96 Jinzhai Road, Hefei, P. R. China
E-mail: zhgu@ustc.edu.cn

Abstract

A palladium/norbornene-catalyzed ortho-silylmethylation reaction using of (iodomethyl)cyclohexyloxydimethylsilane as the electrophile was reported. The ((cyclohexyloxy)dimethylsilyl)methyl group was readily oxidized using the Fleming–Tamao process or by ceric ammonium nitrate to give benzylic alcohol derivatives. This method was successfully applied in a concise synthesis of a biaryl analogue of schisandrins.

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Publication details

The article was received on 12 Oct 2016, accepted on 10 Nov 2016 and first published on 10 Nov 2016

Article type: Communication

DOI: 10.1039/C6CC08227K

Citation: Chem. Commun., 2016,52, 13999-14002

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The palladium/norbornene-catalyzed ortho-silylmethylation reaction: a practical protocol for ortho-functionalized one-carbon homologation of aryl iodides

X. Sui, L. Ding and Z. Gu, Chem. Commun., 2016, 52, 13999
DOI: 10.1039/C6CC08227K
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Chemical Communications

The palladium/norbornene-catalyzed ortho-silylmethylation reaction: a practical protocol for ortho-functionalized one-carbon homologation of aryl iodides

Abstract

Supplementary files

Publication details

The palladium/norbornene-catalyzed ortho-silylmethylation reaction: a practical protocol for ortho-functionalized one-carbon homologation of aryl iodides

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