The Synthesis of Internal Conjugated (<i>E</i>)-Enynyldialkylboranes and Their Applications to the Syntheses of Conjugated Alkynones, Conjugated (<i>E</i>)-Enynes, and Conjugated Enynes Bearing an Unsaturated Group on the Double Bond
作者:Masayuki Hoshi、Yuzuru Masuda、Akira Arase
DOI:10.1246/bcsj.58.1683
日期:1985.6
(E)-Enynyldialkylboranes, thus obtained, gave regio- and/or stereospecifically defined corresponding conjugated alkynones by alkaline hydrogen peroxide oxidation, conjugated (E)-enynes by protonolysis with acetic acid, and conjugated enynes bearing an unsaturated group on the internal alkenyl carbon atom by bis(acetylacetonato)copper-catalyzed cross-coupling reaction with allyl bromide or 1-bromo-1-hexyne respectively
Selective Green Coupling of Alkynyltins and Allylic Halides to Trienynes via a Tandem Double Stille Reaction
作者:Isabel Meana、Ana C. Albéniz、Pablo Espinet
DOI:10.1002/adsc.201000430
日期:2010.11.22
The palladium-catalyzed reaction of alkynyltin compounds with allylic chlorides leads to a 2:2 coupling to give trienynes by regio- and stereoselective formation of three new CC bonds. The reaction can be applied to different alkynyl and allylic fragments, providing a wide range of trienynes with different substitution patterns in very good yields. They can be prepared in a green way using recyclable
Internal alkenyldialkylboranes give regio- and stereospecifically designed 1,4-dienes or conjugated enynes, bearing a substituent at the internal alkenyl carbon atom, by a coupling reaction with allylbromide or 1-bromo-1-alkynes.