Palladium-Catalyzed, ortho-Selective C-H Halogenation of Benzyl Nitriles, Aryl Weinreb Amides, and Anilides

被引：61
作者：
Das, Riki [1 ]
Kapur, Manmohan [1 ]
机构：
[1] Indian Inst Sci Educ & Res IISER, Dept Chem, Bhopal 462066, Madhya Pradesh, India
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 02期
关键词：
BOND FORMATION; REGIOSELECTIVE HALOGENATION; WEAK COORDINATION; ORTHO-BROMINATION; ACTIVATION; IODINATION; FUNCTIONALIZATION; CHLORINATION; VERSATILE; ARYLATION;
D O I：
10.1021/acs.joc.6b02731
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A palladium-catalyzed, ortho-selective C-H halogenation methodology is reported herein. The highlight of the work is the highly selective C(sp(2))-H functionalization of benzyl nitriles in the presence of activated C(sp(3))-H bond, which results in good yields of the halogenated products with excellent regioselectivity. Along with benzyl nitriles, aryl Weinreb amides and anilides have been evaluated for the transformation using aprotic conditions. Mechanistic studies yield interesting aspects with respect to the pathway of the reaction and the directing group abilities.
引用
收藏
页码：1114 / 1126
页数：13
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