Palladium-Catalyzed Cross-Coupling in the Synthesis of Pyridinyl Boxazomycin C Analogues

Abstract

[reaction: see text] Palladium-catalyzed cross-coupling of 2-thiomethylbenzoxazoles with tri-alkylstannyl pyridines efficiently produces pyridinyl boxazomycin C analogues.

Transition metals in organic synthesis: Highlights for the year 2005

“…Examples of ring systems include, bromooxabicyclo[3.2.1]octadiene [28], 5-trifloxyindoles [29], 6-halopurines [30] and 3,5-dichloro-2(H)-1,4-oxazin-2-one [31]. A palladium-catalyzed coupling of a 2-thiomethylbenzoxazole with a 2-pyridyltin reagent was used in a synthesis of pyridinyl boxazomycin C analogs [32].…”

Desulfitative Cross-Coupling of Protecting Group-Free 2-Thiouracil Derivatives with Organostannanes

“…In independent studies, our group has shown that the carboxylate counterion is not essential for the catalytic cycle to proceed with stannane derivatives, and can be efficiently replaced by the readily accessible copper(I) bromide−dimethyl sulfide complex (CuBr ·Me 2 S) . This approach has been recently successfully applied to various substrates …”