Remote para-C-H Functionalization of Arenes by a D-Shaped Biphenyl Template-Based Assembly
DSpace at IIT Bombay
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Title |
Remote para-C-H Functionalization of Arenes by a D-Shaped Biphenyl Template-Based Assembly
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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 |
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Subject |
ELECTRON-DEFICIENT ARENES
COPPER-CATALYZED ARYLATION FRUSTRATED LEWIS PAIRS CARBON-HYDROGEN BONDS DIRECTING GROUP SELECTIVE ARYLATION PHENOL DERIVATIVES CARBOXYLIC-ACIDS ACTIVATION OLEFINATION |
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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.
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Publisher |
AMER CHEMICAL SOC
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Date |
2016-01-15T06:27:07Z
2016-01-15T06:27:07Z 2015 |
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Type |
Article
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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 |
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Language |
en
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