Para-Selective Cyanation of Arenes by H-Bonded Template

Sandeep Pimparkar; Trisha Bhattacharya; Arun Maji; Argha Saha; Ramasamy Jayarajan; Uttam Dutta; Gang Lu; David W. Lupton; Debabrata Maiti

doi:10.1002/chem.202001368

Para-Selective Cyanation of Arenes by H-Bonded Template

Sandeep Pimparkar, Trisha Bhattacharya, Arun Maji, Argha Saha, Ramasamy Jayarajan, Uttam Dutta, Gang Lu, David W. Lupton, Debabrata Maiti

Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

42 Scopus citations

Abstract

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 a 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, which heralds the inception of para-deuteration. The synthetic impact of the methodology was highlighted with reusability of directing group and post synthetic modifications.

Original language	English
Pages (from-to)	11558-11564
Number of pages	7
Journal	Chemistry - A European Journal
Volume	26
Issue number	50
DOIs	https://doi.org/10.1002/chem.202001368
State	Published - Sep 4 2020

Bibliographical note

Publisher Copyright:
© 2020 Wiley-VCH GmbH

Funding

This research is supported by SERB (CRG/2018/003951) India. GL thanks the financial support from National Natural Science Foundation of China (No. 21973055) and the Natural Science Foundation of Shandong Province (ZR2019MB049). Financial support received from IITB-Monash Research Academy (SP and UD), CSIR-India (AM, AS), UGC (TB) and DST-India Fast Track Scheme for RJ (YSS/2014/000530). This research is supported by SERB (CRG/2018/003951) India. GL thanks the financial support from National Natural Science Foundation of China (No. 21973055) and the Natural Science Foundation of Shandong Province (ZR2019MB049). Financial support received from IITB‐Monash Research Academy (SP and UD), CSIR‐India (AM, AS), UGC (TB) and DST‐India Fast Track Scheme for RJ (YSS/2014/000530).

Funders	Funder number
CSIR - Central Food Technological Research Institute India
DST-India	YSS/2014/000530
National Natural Science Foundation of China (NSFC)	21973055
National Natural Science Foundation of China (NSFC)
Research Grants Council, University Grants Committee
Science and Engineering Research Board	CRG/2018/003951
Science and Engineering Research Board
Natural Science Foundation of Shandong Province	ZR2019MB049
Natural Science Foundation of Shandong Province
IITB-Monash Research Academy

Keywords

cyanation
DFT study
H-bonded template
para-C−H activation
regioselectivity

ASJC Scopus subject areas

Catalysis
General Chemistry
Organic Chemistry

Access to Document

10.1002/chem.202001368

Cite this

@article{dc798c3ce59f4ee099895b97c7cc1afd,

title = "Para-Selective Cyanation of Arenes by H-Bonded Template",

abstract = "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 a 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, which heralds the inception of para-deuteration. The synthetic impact of the methodology was highlighted with reusability of directing group and post synthetic modifications.",

keywords = "cyanation, DFT study, H-bonded template, para-C−H activation, regioselectivity",

author = "Sandeep Pimparkar and Trisha Bhattacharya and Arun Maji and Argha Saha and Ramasamy Jayarajan and Uttam Dutta and Gang Lu and Lupton, \{David W.\} and Debabrata Maiti",

note = "Publisher Copyright: {\textcopyright} 2020 Wiley-VCH GmbH",

year = "2020",

month = sep,

day = "4",

doi = "10.1002/chem.202001368",

language = "English",

volume = "26",

pages = "11558--11564",

number = "50",

}

TY - JOUR

T1 - Para-Selective Cyanation of Arenes by H-Bonded Template

AU - Pimparkar, Sandeep

AU - Bhattacharya, Trisha

AU - Maji, Arun

AU - Saha, Argha

AU - Jayarajan, Ramasamy

AU - Dutta, Uttam

AU - Lu, Gang

AU - Lupton, David W.

AU - Maiti, Debabrata

PY - 2020/9/4

Y1 - 2020/9/4

N2 - 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 a 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, which heralds the inception of para-deuteration. The synthetic impact of the methodology was highlighted with reusability of directing group and post synthetic modifications.

AB - 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 a 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, which heralds the inception of para-deuteration. The synthetic impact of the methodology was highlighted with reusability of directing group and post synthetic modifications.

KW - cyanation

KW - DFT study

KW - H-bonded template

KW - para-C−H activation

KW - regioselectivity

UR - http://www.scopus.com/inward/record.url?scp=85085762768&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85085762768&partnerID=8YFLogxK

U2 - 10.1002/chem.202001368

DO - 10.1002/chem.202001368

M3 - Article

C2 - 32196777

AN - SCOPUS:85085762768

SN - 0947-6539

VL - 26

SP - 11558

EP - 11564

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 50

ER -

Para-Selective Cyanation of Arenes by H-Bonded Template

Abstract

Bibliographical note

Funding

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this