Palladium-Catalyzed Regioselective Silaboration of Pyridines Leading to the Synthesis of Silylated Dihydropyridines

Palladium-Catalyzed Regioselective Silaboration of Pyridines Leading to the Synthesis of Silylated Dihydropyridines
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DOI:
10.1021/ja2020229
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发表时间:
2011-05-18
影响因子:
15
通讯作者:
Suginome, Michinori
Suginome, Michinori
中科院分区:
化学1区
文献类型:
--
作者:
Oshima, Kazuyuki;Ohmura, Toshimichi;Suginome, Michinori

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The addition of silylboronic esters to pyridine takes place in toluene at 50 degrees C in the presence of a palladium catalyst to give N-boryl-4-silyl-1,4-dihydropyridines in high yield. The regioselective 1,4-silaboration also proceeds in the reaction of 2-picoline and 3-substituted pyridines, whereas 4-substituted pyridines undergo 1,2-silaboration to give N-boryl-2-silyl-1,2-dihydropyridines regioselectively.