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

doi:10.1021/ol400035f

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

Syngenta Ltd

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

41 Citations (SciVal)

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 language	English
Pages (from-to)	702-705
Number of pages	4
Journal	Organic Letters
Volume	15
Issue number	3
Early online date	23 Jan 2013
DOIs	https://doi.org/10.1021/ol400035f
Publication status	Published - Feb 2013

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10.1021/ol400035f

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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",

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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 - https://www.scopus.com/pages/publications/84873379696

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

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DO - 10.1021/ol400035f

M3 - Article

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VL - 15

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JO - Organic Letters

JF - Organic Letters

IS - 3

ER -

Iodide as an activating agent for acid chlorides in acylation reactions

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Iodide as an activating agent for acid chlorides in acylation reactions

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