Regio- and stereoselective synthesis of 1,4-enynes by iron-catalysed Suzuki–Miyaura coupling of propargyl electrophiles under ligand-free conditions
Ryosuke Agata, Siming Lu, Hiroshi Matsuda, Katsuhiro Isozaki, Masaharu Nakamura
Abstract
The first iron-catalysed cross coupling of propargyl electrophiles with lithium alkenylborates has been developed. Various propargyl electrophiles can be cross-coupled with lithium (E)- or (Z)-alkenylborates in a stereospecific manner to afford the corresponding 1,4-enynes in good to excellent yields. The reaction features high SN2-type regioselectivity and functional group compatibility.
Topics & Concepts
ChemistryPropargylStereoselectivityElectrophileLigand (biochemistry)Suzuki reactionCoupling (piping)Combinatorial chemistryStereochemistryCatalysisOrganic chemistryPalladiumReceptorMechanical engineeringBiochemistryEngineeringCatalytic Alkyne ReactionsCatalytic Cross-Coupling ReactionsSynthetic Organic Chemistry Methods