A new stereospecific cross-coupling by the palladium-catalyzed reaction of 1-alkenylboranes with 1-alkenyl or 1-alkynyl halides

✍ Scribed by Norio Miyaura; Kinji Yamada; Akira Suzuki

• Publisher: Elsevier Science
• Year: 1979
• Tongue: French
• Weight: 253 KB
• Volume: 20
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)95429-2

✦ Synopsis

Sumnary:

The representative (E)-1-alkenyldisiamylboranes and (E)-1-alkenyl-1,3,2-benzodioxaboroles readily obtainable via hydroboration of 1-alkynes react with 1-alkenyl halides or l-alkynyl halides in the presence of a catalytic amount of tetrakis(triphenylphosphine)palladium and base to give corresponding conjugated (E)-dienes or (E)-enynes with high regio-and stereospecificity in good yields, respectively. Stereoselective syntheses of conjugated (E,E)-and (E,Z)-dienes are of considerable importance in organic chemistry in themselves, as well as in their utilization in other reactions such as the Dieles-Alder reaction. Recently a number of new methods for the preparation of conjugated dienes have appeared utilizing organoaluminum,' boron,2 copper,3 magnesium,4 silver,5 mercury,6