Palladium-catalyzed picolinamide-directed halogenation of ortho C-H bonds of benzylamine substrates

被引：40
|
作者：
Lu, Chengxi [1 ]
Zhang, Shu-Yu [1 ]
He, Gang [1 ]
Nack, William A. [1 ]
Chen, Gong [1 ]
机构：
[1] Penn State Univ, Dept Chem, University Pk, PA 16802 USA
来源：
TETRAHEDRON | 2014年 / 70卷 / 27-28期
关键词：
Palladium; C-H halogenation; Picolinamide; Benzylamine; UNACTIVATED C(SP(3))-H; ORTHO-C(SP(2))-H BONDS; C(SP(2))-H BONDS; IODINATION; EFFICIENT; ALKYLATION; ARYLATION; ARENES; FUNCTIONALIZATION; BROMINATION;
D O I：
10.1016/j.tet.2014.02.070
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We report a new set of methods for the halogenation of the ortho C-H bonds of N-benzyl picolinamides under palladium-catalyzed conditions. These reactions feature the use of a unique combination of K(Na) XO3 and K2S2O8 reagents, which enables the installation of iodo, bromo, and chloro groups onto the ortho position of N-benzyl picolinamides in a unified fashion. A variety of benzylamine products bearing complex halogen substitution can be quickly prepared from much simpler precursors in good yield and selectivity. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码：4197 / 4203
页数：7
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