Novel approach to benzo-fused 1,2-azaphospholene involving a Pd(<scp>ii</scp>)-assisted tandem P–C bond cleavage and P–N bond formation reaction
Harish S. Kunchur, Latchupatula Radhakrishna, Madhusudan K. Pandey, Maravanji S. Balakrishna
Abstract
New bisphosphine o-Ph2PC6H4C(O)N(H)C6H4PPh2-o (1) (Bala-HariPhos) showed a unique reactivity towards Pd(ii) resulting in a 1,2-azaphospholene complex, involving a tandem P-C bond cleavage, P-N bond formation and cyclization process via the elimination of PhH. Mechanistic details were investigated using NMR spectroscopy, DFT calculations and kinetic data, and by SCXRD analysis. It involves the reductive elimination from a tautomerised complex to form a phosphonium salt followed by oxidative addition.
Topics & Concepts
ChemistryCleavage (geology)Bond cleavageMetathesisTandemPeptide bondSalt metathesis reactionStereochemistryAmideMedicinal chemistryRing (chemistry)CatalysisOrganic chemistryMaterials sciencePolymerizationComposite materialFracture (geology)EnzymePolymerSynthetic Organic Chemistry MethodsCatalytic Cross-Coupling ReactionsOrganoboron and organosilicon chemistry