31026-78-5Relevant articles and documents
Palladium(0)-catalyzed [2 + 2 + 1] cyclization of 1,6-enynes with vinyl bromides: A highly diastereoselective synthesis of tetrahydro-1H-cyclopenta [c] furans bearing two quaternary carbon centers
Diao, Yunxia,Zuo, Zhijun,Wang, Hui,Liu, Jingjing,Luan, Xinjun
, p. 4601 - 4608 (2017)
A new cascade process has been accomplished for the synthesis of tetrahydro-1H-cyclopenta[c]furans through palladium-catalyzed [2 + 2 + 1] cyclization of 1,6-enynes with vinyl bromides. Notably, the key feature of this transformation is the use of vinyl bromides as the C1 building block. Various functionalized tetrahydro-1H-cyclopenta[c]furans bearing two quaternary carbon centers could be obtained in good yields with excellent diastereoselectivities.
A Cascade Suzuki-Miyaura/Diels-Alder Protocol: Exploring the Bifunctional Utility of Vinyl Bpin
Cain, David L.,McLaughlin, Calum,Molloy, John J.,Carpenter-Warren, Cameron,Anderson, Niall A.,Watson, Allan J. B.
supporting information, p. 787 - 791 (2019/04/25)
Cascade reactions are an important strategy in reaction design, allowing streamlining of chemical synthesis. Here we report a cascade Suzuki-Miyaura/Diels-Alder reaction, employing vinyl Bpin as a bifunctional reagent in two distinct roles: as an organoboron nucleo phile for cross-coupling and as a Diels-Alder dienophile. Merging these two reactions enables a rapid and operationally simple synthesis of functionalized carbocycles in good yield. The effect of the organoboron subtype on Diels-Alder regioselectivity was investigated and postsynthetic modifications were carried out on a model substrate. The potential for a complementary Heck/Diels-Alder process was also assessed.
A mild synthesis of vinyl halides and gem-dihalides using triphenyl phosphite-halogen-based reagents
Spaggiari, Alberto,Vaccari, Daniele,Davoli, Paolo,Torre, Giovanni,Prati, Fabio
, p. 2216 - 2219 (2007/10/03)
A new application of (PhO)3P-halogen-based reagents to the synthesis of vinyl halides and gem-dihalides is described. Vinyl halides were prepared in good to excellent yields from enolizable ketones, whereas aldehydes afforded the corresponding gem-dihalides. The halogenation proceeded smoothly under mild conditions.