Coupling reactions of heteroarenes with phosphites under silver catalysis.

A silver-catalyzed dehydrogenative cross-coupling reaction of substituted furans, thiophene, thioazole, and pyrrole 1a-e with dialkyl phosphites 2 was first developed to afford corresponding phosphonated products 3a-h with up to 89% yield and good regioselectivities. Moreover, an unprecedented coupling of various substituted pyridines 1f-k with dialkyl phosphites 2 using AgNO(3) as a catalyst and K(2)S(2)O(8) as an oxidant, followed by reduction with Na(2)S(2)O(3), was also realized to furnish desired pyridine phosphonates 3i-q in satisfactory yields with good regioselectivities.