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Remote para-C–H functionalization of arenes by a D-shaped biphenyl template-based assembly

Bag, Sukdev, Patra, Tuhin, Modak, Atanu, Deb, Arghya, Maity, Soham, Dutta, Uttam, Dey, Aniruddha, Kancherla, Rajesh, Maji, Arun, Hazra, Avijit, Bera, Milan and Maiti, Debabrata 2015. Remote para-C–H functionalization of arenes by a D-shaped biphenyl template-based assembly. Journal of the American Chemical Society 137 (37) , pp. 11888-11891. 10.1021/jacs.5b06793

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Site-selective C–H functionalization has emerged as an efficient tool in simplifying the synthesis of complex molecules. Most often, directing group (DG)-assisted metallacycle 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 functionalization 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 o- and m-C–H activation. The applicability of this D-shaped biphenyl template-based strategy is demonstrated by synthesizing various complex molecules.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Publisher: American Chemical Society
ISSN: 0002-7863
Last Modified: 06 May 2023 01:58

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