Recyclable Aliphatic Nitrile-Template Enabled Remote meta-C–H Functionalization at Room Temperature

Ramesh, Perla and Mallik, Bhabani Shankar and Satyanarayana, G. and et al, . (2022) Recyclable Aliphatic Nitrile-Template Enabled Remote meta-C–H Functionalization at Room Temperature. The Journal of Organic Chemistry, 87 (5). pp. 2204-2221. ISSN 0022-3263

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Abstract

This article describes the development of a new aliphatic nitrile-template-directed remote meta-selective C-H olefin functionalization reaction of arenes. Remarkably, unlike the previous reports, this process is feasible at room temperature and enabled the formation of products with excellent regioselectivity. The present protocol encompasses a broad spectrum of substituted dihydrocinnamic acids and olefins, producing meta-C-H olefinated products (up to 96% yield). In addition, the efficacy of the present method has been showcased by the synthesis of various drug analogues (e.g., cholesterol, estrone, ibuprofen, and naproxen). Significantly, the robustness of meta-olefination was also demonstrated by gram-scale synthesis. The new nitrile-based meta-directing template, in particular, could be easily synthesized in two steps and recycled under mild conditions. © 2022 American Chemical Society. All rights reserved.

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IITH Creators:

IITH Creators	ORCiD
Mallik, Bhabani Shankar	http://orcid.org/0000-0001-9657-1497
Satyanarayana, G.	UNSPECIFIED

Item Type:

Article

Additional Information:

We greatly acknowledge the financial support from DST-SERB (Department of Science and Technology, Science and Engineering Research Board, Grant EMR/2017/005312), New Delhi. P.R. thanks DST-SERB for the award of National Postdoctoral Fellowship (Diary SERB/F/7226/2017-2018), C.B.S., D.R., and K.R.G. thank the UGC New Delhi for providing the fellowship. D.S. thanks DST-SERB (EMR/2017/005312) for the research fellowship.

Uncontrolled Keywords:

Aliphatic nitriles; Broad spectrum; C-H functionalization; Condition; Functionalization reactions; Gram-scale synthesis; Naproxens; Olefination; Recyclables; Synthesised

Subjects:

Chemistry

Divisions:

Department of Chemistry

Depositing User:

. LibTrainee 2021

Date Deposited:

22 Jul 2022 06:26

Last Modified:

22 Jul 2022 06:26

URI:

http://raiithold.iith.ac.in/id/eprint/9574