Highly stereoselective and catalytic desulfitative CO and CI dienylation with sulfolenes: The importance of basic additives. Issue 24 (14th June 2019)

• Record Type: Journal Article
• Authors: Dang, Hang T.; Nguyen, Viet D.; Pham, Hoang H.; Arman, Hadi D.; Larionov, Oleg V.
• Is Part Of: Tetrahedron. Volume 75:Issue 24(2019)
• Page Start: 3258
• Page End: 3264
• Publication Date: 2019-06-14
• Subjects: Cross-coupling -- Desulfitation -- Dienes -- Palladium catalysis -- Polyenes -- Sulfinates -- Sulfolenes; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2019.04.012
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: Conjugated dienes and polyenes are central structural motifs of natural products, and key synthetic intermediates in organic synthesis and materials science. We describe herein a palladium-catalyzed dienylation of aryl, heteroaryl, and vinyl triflates, nonaflates and iodides that were previously identified as recalcitrant substrates for the sulfolene-mediated catalytic dienylation. The method has now been successfully expanded to CO and CI dienylation, demonstrating broad scope with respect to sulfonates, iodides and sulfolenes. The reactions proceed with high regio- and stereoselectivity, and efficiency that are strongly influenced by basic additives, whose influence on the reaction performance was systematically studied. Graphical abstract: Image 1