Palladium-catalyzed ortho C-H bond alkylation of benzylamides with alpha-bromo ketones

Song Jiao; Chen Wenbo; Zhao Yunjie; Li Chenglong; Liang Guang; Huang Lehao

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Palladium-catalyzed ortho C-H bond alkylation of benzylamides with alpha-bromo ketones

机译：钯催化的邻苯甲酰酯与α-溴酮苄基键烷基化

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摘要

A Pd-catalyzed alkylation of ortho C-H bonds in benzylamides possessing a bidentate- quinolinamide directing group with alpha-bromo ketones or nitrile is reported. alpha-Bromo aryl ketones, alpha-bromo alkyl ketone, and even alpha-bromo alkyl nitrile are competent reagents in this transformation, providing direct alkylated products with a pendant carbonyl or cyano group. Furthermore, direct alkylated products can be hydrolyzed under acidic conditions, providing a straightforward strategy for preparing high-value 3-arylisoquinoline derivatives.

机译：据报道，苄基酰胺中具有α-溴酮酮或腈的苄基酰胺中的邻苯胺酰基键的PD催化的烷基化烷基化。 α-溴芳基酮，α-溴烷基酮，甚至α-溴烷基丁腈是该转化中具有富有药物，提供具有侧链羰基或氰基的直接烷基化产物。此外，直接烷基化产物可以在酸性条件下水解，提供制备高值3-芳基异喹啉衍生物的直接策略。

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《RSC Advances》 |2016年第60期|共9页
作者
Song Jiao; Chen Wenbo; Zhao Yunjie; Li Chenglong; Liang Guang; Huang Lehao;
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Wenzhou Med Univ Sch Pharmaceut Sci Chem Biol Res Ctr Wenzhou 325035 Zhejiang Peoples R China;

Wenzhou Med Univ Sch Pharmaceut Sci Chem Biol Res Ctr Wenzhou 325035 Zhejiang Peoples R China;

Wenzhou Med Univ Sch Pharmaceut Sci Chem Biol Res Ctr Wenzhou 325035 Zhejiang Peoples R China;

Wenzhou Med Univ Sch Pharmaceut Sci Chem Biol Res Ctr Wenzhou 325035 Zhejiang Peoples R China;

Wenzhou Med Univ Sch Pharmaceut Sci Chem Biol Res Ctr Wenzhou 325035 Zhejiang Peoples R China;

Wenzhou Med Univ Sch Pharmaceut Sci Chem Biol Res Ctr Wenzhou 325035 Zhejiang Peoples R China;

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正文语种 eng
中图分类化学;
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1. Palladium-catalyzed ortho C-H bond alkylation of benzylamides with alpha-bromo ketones [J] . Song Jiao, Chen Wenbo, Zhao Yunjie, RSC Advances . 2016,第60期

机译：钯催化的邻苯甲酰酯与α-溴酮苄基键烷基化
2. Palladium-catalyzed alkylation of ortho-C(sp~2)-H bonds of benzylamide substrates with alkyl halides [J] . Zhao Y., Chen G. Organic letters . 2011,第18期

机译：钯与烷基卤化物催化苄基酰胺底物的邻位C（sp〜2）-H键的烷基化
3. Palladium-catalyzed ortho-selective C-H bond chlorination of aromatic ketones [J] . Gang Shan, Gui-Yi Huang, Yu Rao, 中国化学快报（英文版） . 2015,第010期

机译：钯催化芳族酮的邻位选择性C-H键氯化
4. A Ruthenium-Catalyzed Reaction of Aromatic Ketones with Organoboronic Acid Esters:A New Method for C-C Bond Formation via C-H Bonds Cleavage [C] . Fumitoshi Kakiuchi, Shintaro Kan, Kimitaka Igi, Symposium on Organometallic Chemistry . 2003

机译：芳香酮与有机硼酸酯的芳香酮催化反应：通过C-H键切割的C-C键形成新方法
5. Chelation-assisted palladium-catalyzed activation of C-H bonds: A new avenue for carbon-heteroatom and carbon-carbon bond formation. [D] . Giri, Ramesh. 2009

机译：螯合辅助的钯催化的C-H键活化：形成碳-杂原子和碳-碳键的新途径。
6. Scope and Limitations of Auxiliary-Assisted Palladium-Catalyzed Arylation and Alkylation of sp2 and sp3 C-H Bonds [O] . Enrico T. Nadres, Gerson Ivan Franco Santos, Dmitry Shabashov, -1

机译：sp2和sp3 C-H键的辅助钯催化的芳基化和烷基化的范围和限制
7. Palladium-Catalyzed Alkylation of sp2 and sp3 C-H Bonds with Methylboroxine and Alkylboronic Acids: Two Distinct C-H Activation Pathways [O] . -1

机译：钯 - 催化SP2和SP3 C-H键与甲基硼氧胺和烷基硼酸的键合：两个不同的C-H激活途径

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Palladium-catalyzed ortho C-H bond alkylation of benzylamides with alpha-bromo ketones

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