Versatile chemistry of six-membered NHC with boranes: bromination at sp<sup>3</sup> borane, activation of the B–H bond of HBpin, and ring expansion of NHC
Gargi Kundu, Ruchi Dixit, Srinu Tothadi, Kumar Vanka, Sakya S. Sen
Abstract
While 6-SIDipp cleaves the B–H bond of pinacolborane (HBpin) to afford the desired 1,1-oxidative-addition product (7), it undergoes ring expansion with 9-borabicyclo[3.3.1]nonane (9-BBN), leading to a seven-membered ring (6b).
Topics & Concepts
BoraneBoranesChemistryHalogenationElectrophileReactivity (psychology)Ring (chemistry)Medicinal chemistryAlkylAdductOxidative additionStereochemistryOrganic chemistryBoronCatalysisPathologyAlternative medicineMedicineOrganoboron and organosilicon chemistryN-Heterocyclic Carbenes in Organic and Inorganic ChemistryCatalytic Cross-Coupling Reactions