Heck Coupling with Nonactivated Alkenyl Tosylates and Phosphates: Examples of Effective 1,2-Migrations of the Alkenyl Palladium(II) Intermediates

What the Heck! A catalytic system composed of a Pd complex with a basic, hindered alkyl phosphine ligand is capable of promoting Heck coupling of nonactivated vinyl tosylates and phosphates with electron‐deficient olefins. An unexpected 1,2‐migration of the alkenyl PdII intermediates (see Scheme) le...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2006-05, Vol.45 (20), p.3349-3353
Main Authors: Hansen, Anders L., Ebran, Jean-Philippe, Ahlquist, Mårten, Norrby, Per-Ola, Skrydstrup, Troels
Format: Article
Language:English
Subjects:
1,2‐migration
2-migration
alkenes
Alkenes - chemistry
Catalysis
Cations, Divalent
Heck reaction
Isomerism
Models, Chemical
Palladium - chemistry
phosphates
Phosphates - chemistry
Tosyl Compounds - chemistry
tosylates
Vinyl Compounds - chemistry
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Summary:What the Heck! A catalytic system composed of a Pd complex with a basic, hindered alkyl phosphine ligand is capable of promoting Heck coupling of nonactivated vinyl tosylates and phosphates with electron‐deficient olefins. An unexpected 1,2‐migration of the alkenyl PdII intermediates (see Scheme) leads to the isomerized Heck coupling product.
ISSN:1433-7851
1521-3773
1521-3773
DOI:10.1002/anie.200600442