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.
Key Laboratory of Mesoscopic Chemistry of Ministry of Education, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, People's Republic of China.
Chang-Bing
CB
Xiang
Yong-Jun
YJ
Bian
Xue-Rong
XR
Mao
Zhi-Zhen
ZZ
Huang
D001393:Azoles / Q000737:chemistry*; D002384:Catalysis; D005663:Furans / Q000737:chemistry*; D015394:Molecular Structure; D063065:Organophosphonates / Q000138:chemical synthesis / Q000737:chemistry; D017905:Phosphites / Q000737:chemistry*; D011725:Pyridines / Q000138:chemical synthesis / Q000737:chemistry; D011758:Pyrroles / Q000737:chemistry*; D012834:Silver / Q000737:chemistry*; D013876:Thiophenes / Q000737:chemistry*
D001393:Azoles; D005663:Furans; D063065:Organophosphonates; D017905:Phosphites; D011725:Pyridines; D011758:Pyrroles; D013876:Thiophenes; D012834:Silver; C023666:pyridine