Record Details

Remote para-C-H Functionalization of Arenes by a D-Shaped Biphenyl Template-Based Assembly

DSpace at IIT Bombay

View Archive Info
 
 
Field Value
 
Title Remote para-C-H Functionalization of Arenes by a D-Shaped Biphenyl Template-Based Assembly
 
Creator BAG, S
PATRA, T
MODAK, A
DEB, A
MAITY, S
DUTTA, U
DEY, A
KANCHERLA, R
MAJI, A
HAZRA, A
BERA, M
MAITI, D
 
Subject ELECTRON-DEFICIENT ARENES
COPPER-CATALYZED ARYLATION
FRUSTRATED LEWIS PAIRS
CARBON-HYDROGEN BONDS
DIRECTING GROUP
SELECTIVE ARYLATION
PHENOL DERIVATIVES
CARBOXYLIC-ACIDS
ACTIVATION
OLEFINATION
 
Description Site-selective C-H functionalization has emerged as an efficient tool in simplifying the synthesis of complex molecules. Most often, directing group (DG)-assisted metallacyde formation serves as an efficient strategy to ensure promising regioselectivity. A wide variety of ortho- and meta-C-H functionalizations stand as examples in this regard. Yet despite this significant progress, DG-assisted selective para-C-H functionalizalion in arenes has remained unexplored, mainly because it involves the formation of a geometrically constrained metallacyclic transition state. Here we report an easily recyclable, novel Si-containing biphenyl-based template that directs efficient functionalization of the distal p-C-H bond of toluene by forming a D-shaped assembly. This DG allows the required flexibility to support the formation of an oversized pre-transition state. By overcoming electronic and steric bias, para-olefination and acetoxylation were successfully performed while undermining oand m-C-H activation. The applicability of this D-shaped biphenyl template-based strategy is demonstrated by synthesizing various complex molecules.
 
Publisher AMER CHEMICAL SOC
 
Date 2016-01-15T06:27:07Z
2016-01-15T06:27:07Z
2015
 
Type Article
 
Identifier JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 137(37)11888-11891
0002-7863
http://dx.doi.org/10.1021/jacs.5b06793
http://dspace.library.iitb.ac.in/jspui/handle/100/17930
 
Language en