Benzamide synthesis by direct electrophilic aromatic substitution with cyanoguanidine

Rajasekhar Reddy Naredla; Douglas A. Klumpp

doi:10.1016/j.tetlet.2012.06.135

Benzamide synthesis by direct electrophilic aromatic substitution with cyanoguanidine

Rajasekhar Reddy Naredla, Douglas A. Klumpp

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

17 Scopus citations

Abstract

Cyanoguanidine is an inexpensive commodity chemical and it is found to be a useful reagent for the direct Friedel-Crafts carboxamidation of arenes. The reaction works best in an excess of Bronsted superacid, an observation suggesting the involvement of a superelectrophilic intermediate. Theoretical calculations indicate that the most stable diprotonated species involves protonation at the guanidine and cyano nitrogen atoms.

Original language	English (US)
Pages (from-to)	4779-4781
Number of pages	3
Journal	Tetrahedron Letters
Volume	53
Issue number	35
DOIs	https://doi.org/10.1016/j.tetlet.2012.06.135
State	Published - Aug 29 2012
Externally published	Yes

Bibliographical note

Funding Information:
We gratefully acknowledge the support of the NIH- National Institute of General Medical Sciences ( GM085736-01A1 ).

Keywords

Benzamide
Carboxamidation
Friedel-Crafts
Superacid
Superelectrophile

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title = "Benzamide synthesis by direct electrophilic aromatic substitution with cyanoguanidine",

abstract = "Cyanoguanidine is an inexpensive commodity chemical and it is found to be a useful reagent for the direct Friedel-Crafts carboxamidation of arenes. The reaction works best in an excess of Bronsted superacid, an observation suggesting the involvement of a superelectrophilic intermediate. Theoretical calculations indicate that the most stable diprotonated species involves protonation at the guanidine and cyano nitrogen atoms.",

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author = "Naredla, {Rajasekhar Reddy} and Klumpp, {Douglas A.}",

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AU - Naredla, Rajasekhar Reddy

AU - Klumpp, Douglas A.

N1 - Funding Information: We gratefully acknowledge the support of the NIH- National Institute of General Medical Sciences ( GM085736-01A1 ).

PY - 2012/8/29

Y1 - 2012/8/29

N2 - Cyanoguanidine is an inexpensive commodity chemical and it is found to be a useful reagent for the direct Friedel-Crafts carboxamidation of arenes. The reaction works best in an excess of Bronsted superacid, an observation suggesting the involvement of a superelectrophilic intermediate. Theoretical calculations indicate that the most stable diprotonated species involves protonation at the guanidine and cyano nitrogen atoms.

AB - Cyanoguanidine is an inexpensive commodity chemical and it is found to be a useful reagent for the direct Friedel-Crafts carboxamidation of arenes. The reaction works best in an excess of Bronsted superacid, an observation suggesting the involvement of a superelectrophilic intermediate. Theoretical calculations indicate that the most stable diprotonated species involves protonation at the guanidine and cyano nitrogen atoms.

KW - Benzamide

KW - Carboxamidation

KW - Friedel-Crafts

KW - Superacid

KW - Superelectrophile

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Benzamide synthesis by direct electrophilic aromatic substitution with cyanoguanidine

Abstract

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Keywords

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