Synthesis of ethoxy dibenzooxaphosphorin oxides through palladium-catalyzed C(sp²)–H activation/C–O formation

Abstract

SummaryWe report an efficient Pd-catalyzed C(sp2)–H activation/C–O bond formation for the synthesis of ethoxy dibenzooxaphosphorin oxides from 2-(aryl)arylphosphonic acid monoethyl esters under aerobic conditions.

DFT Studies on the Mechanism of Palladium(IV)-Mediated C–H Activation Reactions: Oxidant Effect and Regioselectivity

“…Current development of palladium catalysis has resulted in many types of C–H functionalizations that diversified traditional group-transfer reactions . Up to now, C–H activation transformations catalyzed by common oxidation-state palladium (Pd 0 and Pd II ) have been much discussed both experimentally and theoretically, , while details on the corresponding Pd IV -mediated pathway were relatively deficient.…”

Rhodium-Catalyzed Cyclocarbonylation of Ketimines via C–H Bond Activation

“…First, we probed the nature of the aromatic C–H bond activation step by an intramolecular competition experiment using monodeuterated imine D 1 - 1a , which exhibited an inverse KIE of 0.7 (Scheme a). This result indicated that the C–H bond metalation is reversible . On the other hand, an intermolecular competition reaction of ketimine 1a and its pentadeuterated analogue D 5 - 1a exhibited a KIE of 2.4 (Scheme b).…”

Synthesis and Chemical Properties of 3-Phosphono-coumarins and 1,2-Benzoxaphosphorins as Precursors for Bioactive Compounds

“…Intramolecular Pd-catalyzed oxidative-cyclization reaction for the formation of 1,2-oxaphosphorine derivatives 69 involving ethyl 2-(phenyl)phenylphosphonate and substituted alkyl 2-(aryl)arylphosphonates 68 was presented by Lee et al [79]. The best reaction conditions included a combination of 10 mol % Pd(OAc) 2 and two equiv.…”