Issue 97, 2016

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

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.

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

Supplementary files

Article information

Article type
Communication
Submitted
12 Oct 2016
Accepted
10 Nov 2016
First published
10 Nov 2016

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

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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