Ruthenium(II) porphyrin-catalyzed amidation of aromatic heterocycles

Ling He; Philip Wai Hong Chan; Wai Man Tsui; Wing Yiu Yu; Chi Ming Che

doi:10.1021/ol049232j

Ruthenium(II) porphyrin-catalyzed amidation of aromatic heterocycles

Ling He, Philip Wai Hong Chan, Wai Man Tsui, Wing Yiu Yu, Chi Ming Che

Research output: Journal article publication › Journal article › Academic research › peer-review

74 Citations (Scopus)

Abstract

(Equation Presented) Ruthenium(II) porphyrin-catalyzed amidation of aromatic heterocycles with iminoiodanes under mild conditions (CH2Cl2, 4 Å molecular sieves, ultrasound, 40°C) was achieved in moderate to good yields (up to 84%) and conversions (up to 99%). Only the N,N-ditosylamidated product was obtained for reactions involving heteroarenes, where X = O, S, or NTs. N-Alkyl- and N-aryl-substituted pyrroles, on the other hand, were shown to give the 3,4-diaminated adduct.

Original language	English
Pages (from-to)	2405-2408
Number of pages	4
Journal	Organic Letters
Volume	6
Issue number	14
DOIs	https://doi.org/10.1021/ol049232j
Publication status	Published - 8 Jul 2004
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol049232j

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title = "Ruthenium(II) porphyrin-catalyzed amidation of aromatic heterocycles",

abstract = "(Equation Presented) Ruthenium(II) porphyrin-catalyzed amidation of aromatic heterocycles with iminoiodanes under mild conditions (CH2Cl2, 4 {\AA} molecular sieves, ultrasound, 40°C) was achieved in moderate to good yields (up to 84%) and conversions (up to 99%). Only the N,N-ditosylamidated product was obtained for reactions involving heteroarenes, where X = O, S, or NTs. N-Alkyl- and N-aryl-substituted pyrroles, on the other hand, were shown to give the 3,4-diaminated adduct.",

author = "Ling He and Chan, {Philip Wai Hong} and Tsui, {Wai Man} and Yu, {Wing Yiu} and Che, {Chi Ming}",

year = "2004",

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T1 - Ruthenium(II) porphyrin-catalyzed amidation of aromatic heterocycles

AU - He, Ling

AU - Chan, Philip Wai Hong

AU - Tsui, Wai Man

AU - Yu, Wing Yiu

AU - Che, Chi Ming

PY - 2004/7/8

Y1 - 2004/7/8

N2 - (Equation Presented) Ruthenium(II) porphyrin-catalyzed amidation of aromatic heterocycles with iminoiodanes under mild conditions (CH2Cl2, 4 Å molecular sieves, ultrasound, 40°C) was achieved in moderate to good yields (up to 84%) and conversions (up to 99%). Only the N,N-ditosylamidated product was obtained for reactions involving heteroarenes, where X = O, S, or NTs. N-Alkyl- and N-aryl-substituted pyrroles, on the other hand, were shown to give the 3,4-diaminated adduct.

AB - (Equation Presented) Ruthenium(II) porphyrin-catalyzed amidation of aromatic heterocycles with iminoiodanes under mild conditions (CH2Cl2, 4 Å molecular sieves, ultrasound, 40°C) was achieved in moderate to good yields (up to 84%) and conversions (up to 99%). Only the N,N-ditosylamidated product was obtained for reactions involving heteroarenes, where X = O, S, or NTs. N-Alkyl- and N-aryl-substituted pyrroles, on the other hand, were shown to give the 3,4-diaminated adduct.

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U2 - 10.1021/ol049232j

DO - 10.1021/ol049232j

M3 - Journal article

SN - 1523-7060

VL - 6

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EP - 2408

JO - Organic Letters

JF - Organic Letters

IS - 14

ER -

Ruthenium(II) porphyrin-catalyzed amidation of aromatic heterocycles

Abstract

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