Alkyl Group Migration in Ni-Catalyzed Conjunctive Coupling with C(sp<sup>3</sup>) Electrophiles: Reaction Development and Application to Targets of Interest
S. Koo, Alex J. Vendola, Sarah N. Momm, James P. Morken
Abstract
A catalytic conjunctive cross-coupling reaction is developed that allows the construction of chiral organoboronic esters from alkylboron ate complexes and alkyl iodide electrophiles. The process occurs most efficiently with a Ni/Pybox-comprised catalyst and with an acenapthoquinone-derived boron ligand. Because of the broad functional group tolerance of this reaction, it can be a versatile tool for organic synthesis. Applications to the construction of (R)-coniine and (−)-indolizidine 209D are described.
Topics & Concepts
ElectrophileChemistryAlkylCatalysisLigand (biochemistry)IodideFunctional groupGroup (periodic table)Coupling reactionCombinatorial chemistryOrganic synthesisMedicinal chemistryOrganic chemistryReceptorPolymerBiochemistryOrganoboron and organosilicon chemistryCatalytic Cross-Coupling ReactionsBoron Compounds in Chemistry