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Issue 10, 2016
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Sequential meta-C–H olefination of synthetically versatile benzyl silanes: effective synthesis of meta-olefinated toluene, benzaldehyde and benzyl alcohols

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Abstract

Tremendous progress has been made towards ortho-selective C–H functionalization in the last three decades. However, the activation of distal C–H bonds and their functionalization has remained fairly underdeveloped. Herein, we report sequential meta-C–H functionalization by performing selective mono-olefination and bis-olefination with late stage modification of the C–Si as well as Si–O bonds. Temporary silyl connection was found to be advantageous due to its easy installation, easy removal and wide synthetic diversification.

Graphical abstract: Sequential meta-C–H olefination of synthetically versatile benzyl silanes: effective synthesis of meta-olefinated toluene, benzaldehyde and benzyl alcohols

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Supplementary files

Article information


Submitted
14 Nov 2015
Accepted
02 Dec 2015
First published
02 Dec 2015

This article is Open Access

Chem. Commun., 2016,52, 2027-2030
Article type
Communication
Author version available

Sequential meta-C–H olefination of synthetically versatile benzyl silanes: effective synthesis of meta-olefinated toluene, benzaldehyde and benzyl alcohols

T. Patra, R. Watile, S. Agasti, T. Naveen and D. Maiti, Chem. Commun., 2016, 52, 2027 DOI: 10.1039/C5CC09446A

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