Iodide as an activating agent for acid chlorides in acylation reactions

R.J. Wakeham, J.E. Taylor, S.D. Bull, J.A. Morris, Jonathan M J Williams

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

Acid chlorides can be activated using a simple iodide source to undergo nucleophilic attack from a variety of relatively weak nucleophiles. These include Friedel-Crafts acylation of N-methylpyrroles, N-acylation of sulfonamides, and acylation reactions of hindered phenol derivatives. The reaction is believed to proceed through a transient acid iodide intermediate.
Original languageEnglish
Pages (from-to)702-705
Number of pages4
JournalOrganic Letters
Volume15
Issue number3
Early online date23 Jan 2013
DOIs
Publication statusPublished - Feb 2013

Fingerprint

acylation
Acylation
Iodides
iodides
Chlorides
chlorides
acids
Acids
Nucleophiles
nucleophiles
Sulfonamides
Phenol
phenols
attack
vehicles
Derivatives

Cite this

Iodide as an activating agent for acid chlorides in acylation reactions. / Wakeham, R.J.; Taylor, J.E.; Bull, S.D.; Morris, J.A.; Williams, Jonathan M J.

In: Organic Letters, Vol. 15, No. 3, 02.2013, p. 702-705.

Research output: Contribution to journalArticle

Wakeham, R.J. ; Taylor, J.E. ; Bull, S.D. ; Morris, J.A. ; Williams, Jonathan M J. / Iodide as an activating agent for acid chlorides in acylation reactions. In: Organic Letters. 2013 ; Vol. 15, No. 3. pp. 702-705.
@article{9cb209492c46434b972cc1298aa9a7e8,
title = "Iodide as an activating agent for acid chlorides in acylation reactions",
abstract = "Acid chlorides can be activated using a simple iodide source to undergo nucleophilic attack from a variety of relatively weak nucleophiles. These include Friedel-Crafts acylation of N-methylpyrroles, N-acylation of sulfonamides, and acylation reactions of hindered phenol derivatives. The reaction is believed to proceed through a transient acid iodide intermediate.",
author = "R.J. Wakeham and J.E. Taylor and S.D. Bull and J.A. Morris and Williams, {Jonathan M J}",
year = "2013",
month = "2",
doi = "10.1021/ol400035f",
language = "English",
volume = "15",
pages = "702--705",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "3",

}

TY - JOUR

T1 - Iodide as an activating agent for acid chlorides in acylation reactions

AU - Wakeham, R.J.

AU - Taylor, J.E.

AU - Bull, S.D.

AU - Morris, J.A.

AU - Williams, Jonathan M J

PY - 2013/2

Y1 - 2013/2

N2 - Acid chlorides can be activated using a simple iodide source to undergo nucleophilic attack from a variety of relatively weak nucleophiles. These include Friedel-Crafts acylation of N-methylpyrroles, N-acylation of sulfonamides, and acylation reactions of hindered phenol derivatives. The reaction is believed to proceed through a transient acid iodide intermediate.

AB - Acid chlorides can be activated using a simple iodide source to undergo nucleophilic attack from a variety of relatively weak nucleophiles. These include Friedel-Crafts acylation of N-methylpyrroles, N-acylation of sulfonamides, and acylation reactions of hindered phenol derivatives. The reaction is believed to proceed through a transient acid iodide intermediate.

UR - http://www.scopus.com/inward/record.url?scp=84873379696&partnerID=8YFLogxK

UR - http://dx.doi.org/10.1021/ol400035f

U2 - 10.1021/ol400035f

DO - 10.1021/ol400035f

M3 - Article

VL - 15

SP - 702

EP - 705

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 3

ER -