Polyene cyclization by a double intramolecular heck reaction. A DFT study

David Balcells; Feliu Maseras; Brian A. Keay; Tom Ziegler

doi:10.1021/om034310c

Polyene cyclization by a double intramolecular heck reaction. A DFT study

David Balcells, Feliu Maseras, Brian A. Keay, Tom Ziegler

Department of Chemistry

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

32 Citations (Scopus)

Abstract

The cyclization of aryl polyene triflate catalyzed by a Pd(II)-BINAP complex in a Heck type reaction was studied by density functional theory (DFT) model. The two migratory insertion steps, where the identity of the final reaction products is identified, were focused. The results show the thermodynamic favor of β-elimination on the endo intermediates over the β-elimination on the exo intermediates. The reversibility of the reaction was shown by the results of the β-elimination on the endo intermediates.

Original language	English
Pages (from-to)	2784-2796
Journal	Organometallics
Volume	23
Issue number	11
DOIs	https://doi.org/10.1021/om034310c
Publication status	Published - 24 May 2004

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abstract = "The cyclization of aryl polyene triflate catalyzed by a Pd(II)-BINAP complex in a Heck type reaction was studied by density functional theory (DFT) model. The two migratory insertion steps, where the identity of the final reaction products is identified, were focused. The results show the thermodynamic favor of β-elimination on the endo intermediates over the β-elimination on the exo intermediates. The reversibility of the reaction was shown by the results of the β-elimination on the endo intermediates.",

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AU - Balcells, David

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AU - Keay, Brian A.

AU - Ziegler, Tom

PY - 2004/5/24

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N2 - The cyclization of aryl polyene triflate catalyzed by a Pd(II)-BINAP complex in a Heck type reaction was studied by density functional theory (DFT) model. The two migratory insertion steps, where the identity of the final reaction products is identified, were focused. The results show the thermodynamic favor of β-elimination on the endo intermediates over the β-elimination on the exo intermediates. The reversibility of the reaction was shown by the results of the β-elimination on the endo intermediates.

AB - The cyclization of aryl polyene triflate catalyzed by a Pd(II)-BINAP complex in a Heck type reaction was studied by density functional theory (DFT) model. The two migratory insertion steps, where the identity of the final reaction products is identified, were focused. The results show the thermodynamic favor of β-elimination on the endo intermediates over the β-elimination on the exo intermediates. The reversibility of the reaction was shown by the results of the β-elimination on the endo intermediates.

U2 - 10.1021/om034310c

DO - 10.1021/om034310c

M3 - Article

VL - 23

SP - 2784

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JO - Organometallics

JF - Organometallics

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