Beneficial effect of carboxylic acid additives on the Pd-catalyzed intramolecular N-arylation of 2-amino-3-(2-chlorophenylsulfonyl)pyrroles

Perounsack X. Moon; Chad E. Stephens

doi:10.1016/j.tetlet.2013.09.011

Beneficial effect of carboxylic acid additives on the Pd-catalyzed intramolecular N-arylation of 2-amino-3-(2-chlorophenylsulfonyl)pyrroles

Perounsack X. Moon, Chad E. Stephens

Chemistry and Physics

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

4 Scopus citations

Abstract

Carboxylic acid additives have been shown to significantly improve the yield of the Pd-catalyzed intramolecular N-arylation of 2-aminopyrroles containing a 2-chlorophenylsulfonyl group at the 3-position to give a novel tricyclic ring system. Pivalic and phenylacetic acid provided the best yield enhancement, while acetic acid showed moderate enhancement. Other acids showed limited to no enhancement or even a detrimental effect on the reaction.

Original language	English (US)
Pages (from-to)	6226-6229
Number of pages	4
Journal	Tetrahedron Letters
Volume	54
Issue number	46
DOIs	https://doi.org/10.1016/j.tetlet.2013.09.011
State	Published - Nov 13 2013

Keywords

2-Aminopyrrole
Buchwald-Hartwig reaction
Carboxylic acid additive
Intramolecular
N-arylation
Pyrrolo[3,2-b]benzo[1,4]thiazine

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Beneficial effect of carboxylic acid additives on the Pd-catalyzed intramolecular N-arylation of 2-amino-3-(2-chlorophenylsulfonyl)pyrroles",

abstract = "Carboxylic acid additives have been shown to significantly improve the yield of the Pd-catalyzed intramolecular N-arylation of 2-aminopyrroles containing a 2-chlorophenylsulfonyl group at the 3-position to give a novel tricyclic ring system. Pivalic and phenylacetic acid provided the best yield enhancement, while acetic acid showed moderate enhancement. Other acids showed limited to no enhancement or even a detrimental effect on the reaction.",

keywords = "2-Aminopyrrole, Buchwald-Hartwig reaction, Carboxylic acid additive, Intramolecular, N-arylation, Pyrrolo[3,2-b]benzo[1,4]thiazine",

author = "Moon, {Perounsack X.} and Stephens, {Chad E.}",

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T1 - Beneficial effect of carboxylic acid additives on the Pd-catalyzed intramolecular N-arylation of 2-amino-3-(2-chlorophenylsulfonyl)pyrroles

AU - Moon, Perounsack X.

AU - Stephens, Chad E.

PY - 2013/11/13

Y1 - 2013/11/13

N2 - Carboxylic acid additives have been shown to significantly improve the yield of the Pd-catalyzed intramolecular N-arylation of 2-aminopyrroles containing a 2-chlorophenylsulfonyl group at the 3-position to give a novel tricyclic ring system. Pivalic and phenylacetic acid provided the best yield enhancement, while acetic acid showed moderate enhancement. Other acids showed limited to no enhancement or even a detrimental effect on the reaction.

AB - Carboxylic acid additives have been shown to significantly improve the yield of the Pd-catalyzed intramolecular N-arylation of 2-aminopyrroles containing a 2-chlorophenylsulfonyl group at the 3-position to give a novel tricyclic ring system. Pivalic and phenylacetic acid provided the best yield enhancement, while acetic acid showed moderate enhancement. Other acids showed limited to no enhancement or even a detrimental effect on the reaction.

KW - 2-Aminopyrrole

KW - Buchwald-Hartwig reaction

KW - Carboxylic acid additive

KW - Intramolecular

KW - N-arylation

KW - Pyrrolo[3,2-b]benzo[1,4]thiazine

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DO - 10.1016/j.tetlet.2013.09.011

M3 - Article

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SN - 0040-4039

VL - 54

SP - 6226

EP - 6229

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 46

ER -

Beneficial effect of carboxylic acid additives on the Pd-catalyzed intramolecular N-arylation of 2-amino-3-(2-chlorophenylsulfonyl)pyrroles

Abstract

Keywords

ASJC Scopus subject areas

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