A broadly applicable quantitative relative reactivity model for nucleophilic aromatic substitution (S<sub>N</sub>Ar) using simple descriptors-Reference-Cited by-同舟云学术

A broadly applicable quantitative relative reactivity model for nucleophilic aromatic substitution (S_NAr) using simple descriptors

Published:2022 Issue:43 Volume:13 Page:12681-12695
ISSN:2041-6520
Container-title:Chemical Science
language:en
Short-container-title:Chem. Sci.

Author:

Lu Jingru¹,Paci Irina¹^ORCID,Leitch David C.¹^ORCID

Affiliation:

1. Department of Chemistry, University of Victoria, 3800 Finnerty Rd. Victoria BC, CANADA, V8P 5C2

Abstract

A model for SNAr reactivity is reported, built from relative rate data obtained by competition studies. Based only on molecular descriptors of the electrophile, the model predicts relative reactivity and site selectivity for many complex substrates.

Funder

Natural Sciences and Engineering Research Council of Canada

Publisher

Royal Society of Chemistry (RSC)

Subject

General Chemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2022/SC/D2SC04041G

Reference135 articles.

1. R. C.Larock , Comprehensive Organic Transformations: A Guide to Functional Group Preparations ; Wiley , 2018

2. E. J.Corey and X.-M.Cheng , The Logic of Chemical Synthesis , John Wiley & Sons , Nashville, TN , 1995

3. The Art of Writing Reasonable Organic Reaction Mechanisms , ed., R. B. Grossman , Springer : New York, NY , 2003

4. Scales of Nucleophilicity and Electrophilicity: A System for Ordering Polar Organic and Organometallic Reactions

5. π-Nucleophilicity in Carbon−Carbon Bond-Forming Reactions

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