Unexpected E-to-Z Isomerizations during the Negishi-Type Homocoupling of E-Iodoalkenes

The direct insertion of Zn into olefin–halide bonds is a challenge. When (E)-alkenyl iodides were treated with a very large excess of Zn nanoparticles, in the presence of Pd(PPh3)4, the dimerization was observed but, unexpectedly, yielding mainly Z,E-1,3-dienes. This apparently contrathermodynamic E-to-Z isomerization of organometallic intermediates is predicted to be general and is explained with the aid of DFT [principally M06/6-311+G(d,p)], MP2, and CCSD(T) calculations.

Publication Details

Journal
Dipòsit Digital de la Universitat de Barcelona (Universitat de Barcelona)
Published
2024-12-01
Primary Topic
Catalytic Cross-Coupling Reactions
Type
article
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article

Unexpected E-to-Z Isomerizations during the Negishi-Type Homocoupling of E-Iodoalkenes

Dipòsit Digital de la Universitat de Barcelona (Universitat de Barcelona)
Catalytic Cross-Coupling Reactions
article

Unexpected E-to-Z Isomerizations during the Negishi-Type Homocoupling of E-Iodoalkenes

article en

Abstract

The direct insertion of Zn into olefin–halide bonds is a challenge. When (E)-alkenyl iodides were treated with a very large excess of Zn nanoparticles, in the presence of Pd(PPh3)4, the dimerization was observed but, unexpectedly, yielding mainly Z,E-1,3-dienes. This apparently contrathermodynamic E-to-Z isomerization of organometallic intermediates is predicted to be general and is explained with the aid of DFT [principally M06/6-311+G(d,p)], MP2, and CCSD(T) calculations.

Dipòsit Digital de la Universitat de Barcelona (Universitat de Barcelona)
Clean water and sanitation
Openalex Percentile: Top 56%
Catalytic Cross-Coupling Reactions
Open Access PDFOpenAlex
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Unexpected E-to-Z Isomerizations during the Negishi-Type Homocoupling of E-Iodoalkenes · Dipòsit Digital de la Universitat de Barcelona (Universitat de Barcelona) (2024) | TGRS Research Map | TGRS