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Synthesis of Imidates : TFA-Mediated Regioselective Amide Alkylation Using Meerwein's Reagent

Popov, Kirill LU and Somfai, Peter LU (2016) In Journal of Organic Chemistry 81(8). p.3470-3472
Abstract

Regioselective O-alkylation of an amide to form the corresponding imidate is a common synthetic problem, often resulting in varying amounts of N-alkylation. Screening existing methods for converting amides to imidates gave inconsistent or irreproducible results, sometimes affording N-alkylamide as the major product. A simple and reliable protocol for amide O-alkylation with complete regioselectivity has been designed, and its scope and efficiency demonstrated on a number of substrates.

Please use this url to cite or link to this publication:
author
and
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Journal of Organic Chemistry
volume
81
issue
8
pages
3 pages
publisher
The American Chemical Society (ACS)
external identifiers
  • pmid:27019206
  • wos:000374436900048
  • scopus:84966318845
ISSN
0022-3263
DOI
10.1021/acs.joc.6b00424
language
English
LU publication?
yes
id
dce8ca31-b406-4e82-ab71-b65165a44465
date added to LUP
2016-06-23 08:30:22
date last changed
2025-10-14 10:04:47
@article{dce8ca31-b406-4e82-ab71-b65165a44465,
  abstract     = {{<p>Regioselective O-alkylation of an amide to form the corresponding imidate is a common synthetic problem, often resulting in varying amounts of N-alkylation. Screening existing methods for converting amides to imidates gave inconsistent or irreproducible results, sometimes affording N-alkylamide as the major product. A simple and reliable protocol for amide O-alkylation with complete regioselectivity has been designed, and its scope and efficiency demonstrated on a number of substrates.</p>}},
  author       = {{Popov, Kirill and Somfai, Peter}},
  issn         = {{0022-3263}},
  language     = {{eng}},
  month        = {{04}},
  number       = {{8}},
  pages        = {{3470--3472}},
  publisher    = {{The American Chemical Society (ACS)}},
  series       = {{Journal of Organic Chemistry}},
  title        = {{Synthesis of Imidates : TFA-Mediated Regioselective Amide Alkylation Using Meerwein's Reagent}},
  url          = {{http://dx.doi.org/10.1021/acs.joc.6b00424}},
  doi          = {{10.1021/acs.joc.6b00424}},
  volume       = {{81}},
  year         = {{2016}},
}