A Dual CuH- and Pd-Catalyzed Stereoselective Synthesis of Highly Substituted 1,3-Dienes
Chuan‐Jin Hou, Alexander W. Schuppe, James Levi Knippel, Anton Ni, Stephen L. Buchwald
Abstract
Conjugated dienes are versatile building blocks and prevalent substructures in synthetic chemistry. Herein, we report a method for the stereoselective hydroalkenylation of alkynes, utilizing readily available enol triflates. We leveraged an in situ-generated and geometrically pure vinyl-Cu(I) species to form the Z,Z- or Z,E-1,3-dienes in excellent stereoselectivity and yield. This approach allowed for the synthesis of highly substituted Z-dienes, including pentasubstituted 1,3-dienes, which are difficult to prepare by existing approaches.
Topics & Concepts
StereoselectivityChemistryCatalysisYield (engineering)EnolConjugated systemCombinatorial chemistryOrganic chemistryPolymerMaterials scienceMetallurgyCatalytic C–H Functionalization MethodsCatalytic Alkyne ReactionsAsymmetric Hydrogenation and Catalysis