Improved turnover numbers in palladium-catalyzed bisdiene cyclization-trapping using N-heterocyclic carbene ligands

James M. Takacs; Suman Layek; Hector Palencia; Ross N. Andrews

doi:10.1002/adsc.200505136

Improved turnover numbers in palladium-catalyzed bisdiene cyclization-trapping using N-heterocyclic carbene ligands

James M. Takacs, Suman Layek, Hector Palencia, Ross N. Andrews

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

5 Scopus citations

Abstract

An optimized palladium-N-heterocyclic carbene catalyst system effects the palladium-catalyzed bisdiene cyclization-trapping with phenol at the 0.01% catalyst loading level with a TON of 7.6 × 10³ and TOF of 280 h^-1, values much higher than typically found for this and related carbocyclizations. The reaction scales well and the trans-substituted six-membered ring product is obtained in excellent yield on a 10-mmole scale without further optimization of the catalyst system or reaction conditions.

Original language	English (US)
Pages (from-to)	1937-1942
Number of pages	6
Journal	Advanced Synthesis and Catalysis
Volume	347
Issue number	15
DOIs	https://doi.org/10.1002/adsc.200505136
State	Published - Dec 2005

Keywords

C-C coupling
Cyclization
Homogeneous catalysis
N-heterocyclic carbenes
Palladium

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/adsc.200505136

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title = "Improved turnover numbers in palladium-catalyzed bisdiene cyclization-trapping using N-heterocyclic carbene ligands",

abstract = "An optimized palladium-N-heterocyclic carbene catalyst system effects the palladium-catalyzed bisdiene cyclization-trapping with phenol at the 0.01% catalyst loading level with a TON of 7.6 × 103 and TOF of 280 h-1, values much higher than typically found for this and related carbocyclizations. The reaction scales well and the trans-substituted six-membered ring product is obtained in excellent yield on a 10-mmole scale without further optimization of the catalyst system or reaction conditions.",

keywords = "C-C coupling, Cyclization, Homogeneous catalysis, N-heterocyclic carbenes, Palladium",

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T1 - Improved turnover numbers in palladium-catalyzed bisdiene cyclization-trapping using N-heterocyclic carbene ligands

AU - Takacs, James M.

AU - Layek, Suman

AU - Palencia, Hector

AU - Andrews, Ross N.

PY - 2005/12

Y1 - 2005/12

N2 - An optimized palladium-N-heterocyclic carbene catalyst system effects the palladium-catalyzed bisdiene cyclization-trapping with phenol at the 0.01% catalyst loading level with a TON of 7.6 × 103 and TOF of 280 h-1, values much higher than typically found for this and related carbocyclizations. The reaction scales well and the trans-substituted six-membered ring product is obtained in excellent yield on a 10-mmole scale without further optimization of the catalyst system or reaction conditions.

AB - An optimized palladium-N-heterocyclic carbene catalyst system effects the palladium-catalyzed bisdiene cyclization-trapping with phenol at the 0.01% catalyst loading level with a TON of 7.6 × 103 and TOF of 280 h-1, values much higher than typically found for this and related carbocyclizations. The reaction scales well and the trans-substituted six-membered ring product is obtained in excellent yield on a 10-mmole scale without further optimization of the catalyst system or reaction conditions.

KW - C-C coupling

KW - Cyclization

KW - Homogeneous catalysis

KW - N-heterocyclic carbenes

KW - Palladium

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VL - 347

SP - 1937

EP - 1942

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 15

ER -

Improved turnover numbers in palladium-catalyzed bisdiene cyclization-trapping using N-heterocyclic carbene ligands

Abstract

Keywords

ASJC Scopus subject areas

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