Iridium-Catalyzed Regioselective C(sp3)-H Silylation of 4-Alkylpyridines at the Benzylic Position with Hydrosilanes Leading to 4-(1-Silylalkyl)pyridines

被引:31
作者
Fukumoto, Yoshiya [1 ]
Hirano, Masaya [1 ]
Chatani, Naoto [1 ]
机构
[1] Osaka Univ, Dept Appl Chem, Fac Engn, Suita, Osaka 5650871, Japan
关键词
C-H functionalization; silylation; 4-alkylpyridine; hydrosilane; iridium catalyst; C-H SILYLATION; TRANSITION-METAL-COMPLEXES; DEHYDROGENATIVE SILYLATION; AROMATIC-SUBSTITUTION; DIHYDROGEN COMPLEXES; BOND ACTIVATION; ARENES; FUNCTIONALIZATION; PALLADIUM; PYRIDINES;
D O I
10.1021/acscatal.7b00539
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The regioselective silylation of C(sp(3))-H bonds at the benzylic position in 4-alkylpyridines with hydrosilanes is described. The reaction proceeds in the presence of a catalytic amount of Ir-4(CO)(12) or Ir(acac)(CO)(2), which possess CO as a ligand, or [Ir(OMe)(cod)](2) under 1 atm of CO. After optimizing the reaction conditions, by using other pyridine derivatives, such as 3,5-dimethylpyridine, as additives, the low product yields of 2-substituted 4-methylpyridines were improved markedly.
引用
收藏
页码:3152 / 3156
页数:5
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