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Catalyzed cross-coupling of allyl bromides with allyl tin reagents

✍ Scribed by James Godschalx; J.K. Stille

Publisher
Elsevier Science
Year
1980
Tongue
French
Weight
224 KB
Volume
21
Category
Article
ISSN
0040-4039

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✦ Synopsis

The reaction of ally1 bromides with ally1 tin reagents, catalyzed by palladium or zinc chloride gives cross-coupled products without allylic transpostion in the ally1 halide partner but with predominate allylic rearrangement from the tin partner.

The synthesis of compounds containing the polyisoprenoid structure by the cross-coupling reactions of allylic segments suffers from the lack of a good general procedure.

πŸ“œ SIMILAR VOLUMES

Cross-coupling reaction of allyl bromide
Cross-coupling reaction of allyl bromides with organotin reagents catalyzed by zinc chloride
✍ J.P. Godschalx; J.K. Stille πŸ“‚ Article πŸ“… 1983 πŸ› Elsevier Science 🌐 French βš– 188 KB

Myrcene and e-farnesene have been synthesized by the zinc chloride catalyzed coupling reaction of (2-methylene-3-butenyl)trimethyltin with prenyl bromide and geranyl bromide, respectively; vitamin K1 was synthesized by a similar coupling reaction. The palladium catalyzed cross-coupling reaction of a