N-heterocyclic carbene-palladium catalysts for the bisdiene cyclization-trapping reaction with sulfonamides under thermal and microwave conditions

James M. Takacs; Somasundaram Venkataraman; Ross N. Andrews; Libbie S.W. Pelter

doi:10.1016/j.jorganchem.2005.08.048

N-heterocyclic carbene-palladium catalysts for the bisdiene cyclization-trapping reaction with sulfonamides under thermal and microwave conditions

James M. Takacs, Somasundaram Venkataraman, Ross N. Andrews, Libbie S.W. Pelter

Chemistry

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

9 Scopus citations

Abstract

Simple palladium-N-heterocyclic carbene catalysts readily effect the palladium-catalyzed cyclization-trapping of bisdienes with sulfonamides. The reaction is quite efficient for a variety of sulfonamides and several bisdienes. For example, using 0.1% of the in situ generated or preformed (IMes)Pd(η³-C₃H₅)Cl complex, the cyclization-trapping of a simple bisdiene with TsN(H)CH₂Ph proceeds in good yield under thermal conditions (74-75%, 75 °C, 9 h). The same reaction run under microwave irradiation proceeds somewhat faster and in even higher yield (86%, 75 °C, 2.5 h).

Original language	English (US)
Pages (from-to)	6205-6209
Number of pages	5
Journal	Journal of Organometallic Chemistry
Volume	690
Issue number	24-25
DOIs	https://doi.org/10.1016/j.jorganchem.2005.08.048
State	Published - Dec 1 2005

Keywords

Catalysis
Microwave irradiation
N-heterocyclic carbene ligands
Palladium

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry
Materials Chemistry

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N-heterocyclic carbene-palladium catalysts for the bisdiene cyclization-trapping reaction with sulfonamides under thermal and microwave conditions. / Takacs, James M.; Venkataraman, Somasundaram; Andrews, Ross N.; Pelter, Libbie S.W.

In: Journal of Organometallic Chemistry, Vol. 690, No. 24-25, 01.12.2005, p. 6205-6209.

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

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title = "N-heterocyclic carbene-palladium catalysts for the bisdiene cyclization-trapping reaction with sulfonamides under thermal and microwave conditions",

abstract = "Simple palladium-N-heterocyclic carbene catalysts readily effect the palladium-catalyzed cyclization-trapping of bisdienes with sulfonamides. The reaction is quite efficient for a variety of sulfonamides and several bisdienes. For example, using 0.1% of the in situ generated or preformed (IMes)Pd(η3-C3H5)Cl complex, the cyclization-trapping of a simple bisdiene with TsN(H)CH2Ph proceeds in good yield under thermal conditions (74-75%, 75 °C, 9 h). The same reaction run under microwave irradiation proceeds somewhat faster and in even higher yield (86%, 75 °C, 2.5 h).",

keywords = "Catalysis, Microwave irradiation, N-heterocyclic carbene ligands, Palladium",

author = "Takacs, {James M.} and Somasundaram Venkataraman and Andrews, {Ross N.} and Pelter, {Libbie S.W.}",

note = "Funding Information: Support from the NSF (CHE-0316825) is gratefully acknowledged. The NMR spectrometers used in this study were purchased with shared instrument Grants (NIH SIG-1-510-RR-06307, NSF CHE-0091975 and NSF MRI-0079750). ",

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doi = "10.1016/j.jorganchem.2005.08.048",

language = "English (US)",

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AU - Takacs, James M.

AU - Venkataraman, Somasundaram

AU - Andrews, Ross N.

AU - Pelter, Libbie S.W.

N1 - Funding Information: Support from the NSF (CHE-0316825) is gratefully acknowledged. The NMR spectrometers used in this study were purchased with shared instrument Grants (NIH SIG-1-510-RR-06307, NSF CHE-0091975 and NSF MRI-0079750).

PY - 2005/12/1

Y1 - 2005/12/1

N2 - Simple palladium-N-heterocyclic carbene catalysts readily effect the palladium-catalyzed cyclization-trapping of bisdienes with sulfonamides. The reaction is quite efficient for a variety of sulfonamides and several bisdienes. For example, using 0.1% of the in situ generated or preformed (IMes)Pd(η3-C3H5)Cl complex, the cyclization-trapping of a simple bisdiene with TsN(H)CH2Ph proceeds in good yield under thermal conditions (74-75%, 75 °C, 9 h). The same reaction run under microwave irradiation proceeds somewhat faster and in even higher yield (86%, 75 °C, 2.5 h).

AB - Simple palladium-N-heterocyclic carbene catalysts readily effect the palladium-catalyzed cyclization-trapping of bisdienes with sulfonamides. The reaction is quite efficient for a variety of sulfonamides and several bisdienes. For example, using 0.1% of the in situ generated or preformed (IMes)Pd(η3-C3H5)Cl complex, the cyclization-trapping of a simple bisdiene with TsN(H)CH2Ph proceeds in good yield under thermal conditions (74-75%, 75 °C, 9 h). The same reaction run under microwave irradiation proceeds somewhat faster and in even higher yield (86%, 75 °C, 2.5 h).

KW - Catalysis

KW - Microwave irradiation

KW - N-heterocyclic carbene ligands

KW - Palladium

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JO - Journal of Organometallic Chemistry

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ER -

N-heterocyclic carbene-palladium catalysts for the bisdiene cyclization-trapping reaction with sulfonamides under thermal and microwave conditions

Abstract

Keywords

ASJC Scopus subject areas

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