RESUMEN
An unprecedented ring-opening cross-coupling of 1,2-oxazetidines with readily available arylboronic acids is achieved for the first time by copper catalysis. Unlike the known electrophilic oxygen reactivity in coupling with organometallic reagents, 1,2-oxazetidines were utilized as formaldimine precursors in this protocol. Remarkable features of this reaction include simple operation, inexpensive catalyst, broad scope and high regioselectivity, delivering a wide array of aminomethylation products. The practicality of this reaction was validated in the one-step downstream transformation of the obtained products into synthetically important molecules and late-stage modification of bioactive acids.
Asunto(s)
Ácidos Borónicos , Cobre , Catálisis , Estructura Molecular , OxígenoRESUMEN
The merger of strain-release of 1,2-oxazetidines with carboxylic acid directed C-H activation in catalytic synthesis of isoindolinones is reported for the first time. This reaction opens a new and sustainable avenue to prepare a range of structurally diverse isoindolinone skeletons from readily available benzoic acids. The success of late-stage functionalization of some bioactive acids, and concise synthesis of biologically important skeletons demonstrated its great synthetic potential in drug discovery. Mechanistic studies indicated a plausible C-H activation/ß-carbon elimination/intramolecular cyclization cascade pathway.