Cross‐Coupling Reaction of Alkenyl Sulfoximines and Alkenyl Aminosulfoxonium Salts with Organozincs by Dual Nickel Catalysis and Lewis Acid Promotion

• Published in: Chemistry : a European journal Vol. 25; no. 35; pp. 8371 - 8386
• Main Authors: Erdelmeier, Irene, Bülow, Gerd, Woo, Chang‐Wan, Decker, Jürgen, Raabe, Gerhard, Gais, Hans‐Joachim
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 21.06.2019; Wiley Subscription Services, Inc
• Subjects: Acceleration; Alcohols; Alkenes; alkenyl sulfoximines; Catalysis; Chemical industry; Chemistry; Chemistry, Multidisciplinary; Coupling; cross-coupling; Diethyl ether; Lewis acid; Magnetic resonance spectroscopy; Nickel; NMR; NMR spectroscopy; Nuclear magnetic resonance; Physical Sciences; Promotion; Reagents; salt promotion; Salts; Science & Technology; Selectivity; Stereoselectivity; Zinc; nickel; CRYSTAL-STRUCTURE ANALYSIS; ENANTIOSELECTIVE SYNTHESIS; alkenyl sulfoximines; HOMOALLYLIC ALCOHOLS; catalysis; HORNER-WADSWORTH-EMMONS; cross-coupling; ASYMMETRIC WITTIG REACTIONS; STEREOSELECTIVE-SYNTHESIS; salt promotion; ALLYLIC SULFOXIMINES; CHIRAL ARSONIUM YLIDES; GRIGNARD-REAGENTS; CONJUGATE ADDITION

In this article, the cross‐coupling reaction (CCR) of exocyclic, axially chiral, and acyclic alkenyl (N‐methyl)sulfoximines with alkyl‐ and arylzincs is described. The CCR generally requires dual Ni catalysis and MgBr2 promotion, which is effective in diethyl ether but not in THF. NMR spectroscopy r...