Formal Olefinic C−H Phosphinylation <i>via</i> Alkenyl Sulfonium Salts
Juan Ma, Jie Lin, Mingrui Li, Liandi Wang, Kaikai Wu, Yong‐Gui Zhou, Zhengkun Yu
Abstract
Abstract Formal olefinic C−P cross‐coupling between alkenyl sulfonium salts and secondary phosphine oxides and H‐phosphinates has been developed. A base enables construction of alkenyl C−P bonds as well as aliphatic C−P bonds at ambient temperature under an air atmosphere. This protocol provides an alternative access to multisubstituted alkenyl phosphine oxides and phosphinates in 40–99% yield from functionalized alkenes through an interrupted Pummerer activation/base‐promoted olefinic C−S bond phosphinylation sequence. Gram‐scale preparation and feasible derivatization demonstrated the applicability of the resultant alkenylphosphine oxides.
Topics & Concepts
ChemistrySulfoniumPhosphineDerivatizationOrganic chemistryBase (topology)ElectrophileMedicinal chemistryPolymer chemistryCatalysisMathematical analysisMathematicsHigh-performance liquid chromatographySalt (chemistry)Sulfur-Based Synthesis TechniquesChemical Synthesis and ReactionsOrganophosphorus compounds synthesis