Highly stereoselective and catalytic desulfitative C-O and C-I dienylation with sulfolenes: The importance of basic additives

TETRAHEDRON

卷:75

Article

Dang, Hang T.¹  Nguyen, Viet D.¹  Pham, Hoang H.¹  Arman, Hadi D.¹  Larionov, Oleg, V¹ 

[1] Univ Texas San Antonio, Dept Chem, San Antonio, TX 78249 USA

关键词: Cross-coupling;    Desulfitation;    Dienes;    Palladium catalysis;    Polyenes;    Sulfinates;    Sulfolenes;   

DOI  :  10.1016/j.tet.2019.04.012

来源: Elsevier

【 摘 要 】

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 C-O and C-I 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. (C) 2019 Elsevier Ltd. All rights reserved.

【 授权许可】

Free