A strictly "pair"-selective synthesis of conjugated diynes via Pd-catalyzed cross coupling of 1,3-diynylzincs: A superior alternative to the Cadiot-Chodkiewicz reaction

Citation
E. Negishi et al., A strictly "pair"-selective synthesis of conjugated diynes via Pd-catalyzed cross coupling of 1,3-diynylzincs: A superior alternative to the Cadiot-Chodkiewicz reaction, ORG LETT, 2(23), 2000, pp. 3687-3689
Citations number
21
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
23
Year of publication
2000
Pages
3687 - 3689
Database
ISI
SICI code
1523-7060(20001116)2:23<3687:AS"SOC>2.0.ZU;2-F
Abstract
[GRAPHICS] A strictly "pair"-selective synthesis of conjugated diynes via Pd-catalyzed cross coupling of 1,3-diynylzincs is described. This method, like the Cadi ot-Chodkiewicz reaction, requires three steps for the synthesis of (RC)-C-1 =CC=CR2 from (RC)-C-1=CH, (RX)-X-2, and HC=CH. However, the high "pair"-sel ectivity permitting high yield production of the desired conjugated diynes without separation of symmetrical diynes promises to make the present proto col superior to the Cadiot-Chodkiewicz reaction in many cases.