Catalytic Synthesis of Heterocycles via the Cleavage of Carbon-Heteroatom Bonds

Abstract

Catalytic synthesis of heteroles via the cleavage of carbon heteroatom bonds is described. The rhodium catalyzed reaction of 2 silylphenylboronic acids with internal alkynes gives 2,3 disubstituted benzosilole derivatives with loss of a substituent in the triorganosilyl group of the staring material. π Extended phospholes and thiophenes were found to be synthesized by the palladium catalyzed reactions of normally unreactive tertiary phosphines and sul des through the cleavage of carbon phosphorus and carbon sulfur bonds, respectively. In addition, double cleavage of carbon phosphorus bonds of bisphosphines is found to occur with the generation of phospholes. Scheme 1. Reported and unreported methods for carbon heteroatom bond formation.

Facile Synthesis of Nitrogen-Containing Six-Membered Benzofuzed Phenophosphazinine Oxides and Studies of the Photophysical Properties

“…They exhibit unique optical and electronic properties and, thus, have widespread applications in organic light-emitting diodes (OLEDs) and other devices . Recently, several novel strategies have recently been developed for the synthesis of five-membered dibenzophospholes. − For instance, the Kawashima group employed the Et 3 B/O 2 -mediated intramolecular radical cyclization of phosphine oxide . This moiety can also be prepared through Pd-catalyzed P–H/C–X and P–H/C–H coupling strategies developed by the Nozaki and Takai group independently.…”