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- Title
Regioselective Transition-Metal-Free Allyl-Allyl Cross-Couplings.
- Authors
Ellwart, Mario; Makarov, Ilya S.; Achrainer, Florian; Zipse, Hendrik; Knochel, Paul
- Abstract
Readily prepared allylic zinc halides undergo SN2-type substitutions with allylic bromides in a 1:1 mixture of THF and DMPU providing 1,5-dienes regioselectively. The allylic zinc species reacts at the most branched end (γ-position) of the allylic system furnishing exclusively γ,α′-allyl-allyl cross-coupling products. Remarkably, the double bond stereochemistry of the allylic halide is maintained during the cross-coupling process. Also several functional groups (ester, nitrile) are tolerated. This cross-coupling of allylic zinc reagents can be extended to propargylic and benzylic halides. DFT calculations show the importance of lithium chloride in this substitution.
- Subjects
REGIOSELECTIVITY (Chemistry); TRANSITION metals; ALLYL compounds; COUPLING reactions (Chemistry); ZINC halides; STEREOCHEMISTRY; FUNCTIONAL groups
- Publication
Angewandte Chemie International Edition, 2016, Vol 55, Issue 35, p10502
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201603923