Electrophilic activation of aminocarboxylic acid by phosphate ester promotes Friedel–Crafts acylation by overcoming charge–charge repulsion-Reference-Cited by-同舟云学术

Electrophilic activation of aminocarboxylic acid by phosphate ester promotes Friedel–Crafts acylation by overcoming charge–charge repulsion

Published:2017 Issue:44 Volume:15 Page:9398-9407
ISSN:1477-0520
Container-title:Organic & Biomolecular Chemistry
language:en
Short-container-title:Org. Biomol. Chem.

Author:

Sumita Akinari¹²³⁴,Otani Yuko¹²³⁴^ORCID,Ohwada Tomohiko¹²³⁴^ORCID

Affiliation:

1. Graduate School of Pharmaceutical Sciences

2. The University of Tokyo

3. Tokyo 113-0033

4. Japan

Abstract

o-Methyl salicylates enhance the reactivity of the phosphate ester via a protonation-induced conformational change to generate acyl phosphate, thereby overwhelming the charge–charge repulsion associated with formation of the acylium ion, enabling aromatic ketones to be generated from various carboxylic acids.

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2017/OB/C7OB02158E

Reference43 articles.

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4. Efficient One‐Pot Friedel–Crafts Acylation of Benzene and its Derivatives with Unprotected Aminocarboxylic Acids in Polyphosphoric Acid

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