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para-Selective Cyanation of Arenes by H-Bonded Template

preprint
submitted on 24.12.2019 and posted on 26.12.2019 by Sandeep Pimparkar, Trisha Bhattacharya, Arun Maji, Argha Saha, Ramasamy Jayarajan, Uttam Dutta, Gang Lu, David Lupton, Debabrata Maiti
The significance of site selective functionalization stands upon the superior selectivity, easy synthesis and diverse product utility. In this work we demonstrate the para-selective introduction of versatile nitrile moiety, enabled by detachable and reusable H-bonded auxiliary. The methodology holds its efficiency irrespective of substrate electronic bias. The conspicuous shift in the step energetics was probed by both experimental and computational mechanistic tools heralds the inception of para-deuteration. The synthetic impact of the methodology was highlighted with reusability of directing group and post synthetic modifications

Funding

SERB (CRG/2018/003951) India

History

Email Address of Submitting Author

dmaiti@iitb.ac.in

Institution

Indian Institute of Technology Bombay.

Country

India

ORCID For Submitting Author

0000-0001-8353-1306

Declaration of Conflict of Interest

Authors declare no conflict of interest.

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in Chemistry - A European Journal

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