Palladium-Catalyzed Direct C-H Silylation and Germanylation of Benzamides and Carboxamides
Palladium-Catalyzed Direct C-H Silylation and Germanylation of Benzamides and Carboxamides
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DOI：
10.1021/ol500519y
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发表时间：
2014-04-04
期刊：
影响因子：
5.2
通讯作者：
Kanai, Motomu
中科院分区：
文献类型：
--
作者：
Kanyiva, Kyalo Stephen;Kuninobu, Yoichiro;Kanai, Motomu
本文报道了以8-氨基喹啉为导向基团，钯催化的苯甲酰胺和羧酰胺的C（sp（2））-H和C（sp（3））-H键的区域选择性活化，然后与乙硅烷偶联得到有机硅烷，产率中等至高。苯甲酰胺的催化C（sp（2））-H锗烷基化反应也在相同的钯催化下进行。该反应耐受各种各样的官能团，并且是可扩展的而不降低产率。通过与肼反应，容易除去和回收双齿导向基团，伴随产生酰基酰肼。
A palladium-catalyzed regioselective activation of C(sp(2))-H and C(sp(3))-H bonds of benzamides and carboxamides, followed by coupling with disilanes to afford organosilanes in moderate to high yields, with the aid of 8-aminoquinoline as a directing group, is reported. Catalytic C(sp(2))-H germanylation of benzamides also proceeds under the same palladium catalysis. The reaction tolerates a wide variety of functional groups and is scalable without yield reduction. The bidentate directing group is readily removed and recovered by the reaction with a hydrazine, with concominant generation of an acyl hydrazide.