Chelation-Assisted Nickel-Catalyzed Oxidative Annulation via Double C-H Activation/Alkyne Insertion Reaction

Castro Luis C. Misal; Obata Atsushi; Aihara Yoshinori; Chatani Naoto

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Chelation-Assisted Nickel-Catalyzed Oxidative Annulation via Double C-H Activation/Alkyne Insertion Reaction

机译：通过双C-H活化/炔烃插入反应的螯合辅助镍催化的氧化环化

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摘要

A nickel/NHC system for regioselective oxidative annulation by double C-H bond activation and concomitant alkyne insertion is described. The catalytic reaction requires a bidentate directing group, such as an 8-aminoquinoline, embedded in the substrate. Various 5,6,7,8-tetrasubstituted-N-(quinolin-8-yl)-1-naphthamides can be prepared as well as phenanthrene and benzo[h]quinoline amide derivatives. Diarylalkynes, dialkylalkynes, and arylalkylalkynes can be used in the system. A Ni-0/Ni-II catalytic cycle is proposed as the main catalytic cycle. The alkyne plays a double role as a two-component coupling partner and as a hydrogen acceptor.

机译：本发明描述了一种镍/ NHC系统，该系统通过双C-H键活化和伴随的炔烃插入来进行区域选择性的氧化环化。催化反应需要嵌入基质中的双齿引导基团，例如8-氨基喹啉。可以制备各种5,6,7,8-四取代-N-（喹啉-8-基）-1-萘酰胺，以及菲和苯并[h]喹啉酰胺衍生物。该系统中可以使用二芳基炔，二烷基炔和芳烷基炔。提出了Ni-0 / Ni-II催化循环作为主要催化循环。炔烃作为两组分偶联伙伴和氢受体起着双重作用。

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来源
《Chemistry: A European journal》 |2016年第4期|共6页
作者
Castro Luis C. Misal; Obata Atsushi; Aihara Yoshinori; Chatani Naoto;
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正文语种 eng
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alkynes; aromatic homologation; C-H activation; chelate-assistance; nickel;

机译：炔烃;芳香族同源;C-H活化;螯合物-辅助;镍;

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1. Chelation-Assisted Nickel-Catalyzed Oxidative Annulation via Double C-H Activation/Alkyne Insertion Reaction [J] . Castro Luis C. Misal, Obata Atsushi, Aihara Yoshinori, Chemistry: A European journal . 2016,第4期

机译：通过双C-H活化/炔烃插入反应的螯合辅助镍催化的氧化环化
2. Rhodium(Ⅲ)-catalyzed cascade oxidative annulation reactions of aryl imidazolium salts with alkynes involving multiple C-H bond activation [J] . Qingmei Ge, Bin Li, Haibin Song, Organic & biomolecular chemistry . 2015,第28期

机译：铑（Ⅲ）催化芳基咪唑鎓盐与炔烃的多级C-H键活化级联氧化反应
3. Mechanistic DFT Study on Rhodium(III)-Catalyzed Double C-H Activation for Oxidative Annulations of 2-Substituted Imidazoles and Alkynes [J] . Xie Peipei, Jia Mengmeng, Xu Xiao-Hua, Asian Journal of Organic Chemistry . 2018,第3期

机译：铑（III）的机械DFT研究 - 催化两种替代二咪唑和炔胺氧化环化合物的双C-H活化
4. Scandium-catalyzed Dearomatic Annulation of Aryl Quinolines with Alkynes via C-H activation [C] . Shao-Jie Lou, Masayoshi Nishiura, Zhaomin Hou 日本化学会春季年会講演予稿集 . 2018

机译：通过C-H激活钪催化芳基喹啉的芳基喹啉的脂肪环节
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. Nickel-catalyzed oxidative C–H/N–H annulation of N-heteroaromatic compounds with alkynes [O] . Atsushi Obata, Akane Sasagawa, Ken Yamazaki, 2019

机译：镍催化的炔烃与N-杂芳族化合物的氧化C–H / N–H环合
7. Nickel-Catalyzed CF/NH Annulation of Aromatic Amides with Alkynes: Activation of CF Bonds under Mild Reaction Conditions [O] . -1

机译：用炔烃的芳族酰胺的镍催化的CF / NH环化：在轻度反应条件下激活CF键
8. Halomethyl-Metal Compounds. LVII. The Insertion of Phenyl (Bromodichloromethyl)Mercury-Derived Dichlorocarbene into C-H Bonds. Further Studies of the Beta-Metal Activated C-H Insertion Reaction. [R] . Seyferth, D., Cheng, Y. M., Traficante, D. D. 1972

机译：卤甲基金属化合物。 LVII。将苯基（溴二氯甲基）汞衍生的二氯卡宾插入C-H键中。 β-金属活化C-H插入反应的进一步研究。

Chelation-Assisted Nickel-Catalyzed Oxidative Annulation via Double C-H Activation/Alkyne Insertion Reaction

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