Palladium-Catalyzed Zinc-Amide-Mediated C-H Arylation of Fluoroarenes and Heteroarenes with Aryl Sulfides

Otsuka Shinya; Yorimitsu Hideki; Osuka Atsuhiro

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Palladium-Catalyzed Zinc-Amide-Mediated C-H Arylation of Fluoroarenes and Heteroarenes with Aryl Sulfides

机译：钯催化的芳烃硫化物介导的氟代芳烃和杂芳烃的Z-酰胺化C-H芳基化

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摘要

C-H arylation of polyfluoroarenes and heteroarenes with aryl sulfides proceeds smoothly with the aid of a palladium-N-heterocyclic carbene catalyst. A bulky zinc amide, TMPZnCl center dot LiCl, plays a key role as an effective base to generate the corresponding arylzinc species in situ. This arylation protocol is practically much easier to perform than our previous method, which necessitates preparation of the arylzinc reagents in advance from the corresponding aryl halides. Aryl sulfides that are prepared through sulfur-specific reactions, such as SNAr sulfanylation and extended Pummerer reactions, undergo this direct arylation, offering interesting transformations that are otherwise difficult to achieve with conventional halogen-based organic synthesis.

机译：借助于钯-N-杂环卡宾催化剂，多氟芳烃和杂芳烃与芳基硫醚的C-H芳基化反应顺利进行。庞大的酰胺锌，TMPZnCl中心点LiCl，在现场产生相应的芳基锌物种方面起着重要的作用。该芳基化方案实际上比我们以前的方法更容易执行，后者需要从相应的芳基卤化物预先制备芳基锌试剂。通过特定于硫的反应（例如SNAr磺酰化和扩展的Pummerer反应）制备的芳基硫化物会经历这种直接芳基化，从而提供有趣的转化，而这些转化是传统的基于卤素的有机合成难以实现的。

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《Chemistry: A European journal》 |2015年第42期|共5页
作者
Otsuka Shinya; Yorimitsu Hideki; Osuka Atsuhiro;
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C-H arylation; C-S bond activation; organosulfur compounds; organozinc compounds; palladium;

机译：C-H芳基化;C-S键活化;有机硫化合物;有机锌化合物;钯;

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1. Palladium-Catalyzed Zinc-Amide-Mediated C-H Arylation of Fluoroarenes and Heteroarenes with Aryl Sulfides [J] . Otsuka Shinya, Yorimitsu Hideki, Osuka Atsuhiro Chemistry: A European journal . 2015,第42期

机译：钯催化的芳烃硫化物介导的氟代芳烃和杂芳烃的Z-酰胺化C-H芳基化
2. Synthesis of multiply arylated heteroarenes, including bioactive derivatives, via palladium-catalyzed direct C-H arylation of heteroarenes with (pseudo)aryl halides or aryliodonium salts [J] . RossiR., BellinaF., LessiM., Synthesis: International Journal of Methods in Synthetic Organic Chemistry . 2014,第21期

机译：通过钯催化杂芳烃与（伪）芳基卤化物或芳基碘鎓盐的直接C-H芳基化反应，合成包括生物活性衍生物在内的多芳基化杂芳基
3. Synthesis of multiply arylated heteroarenes, including bioactive derivatives, via palladium-catalyzed direct C-H arylation of heteroarenes with (pseudo)aryl halides or aryliodonium salts [J] . RossiR., BellinaF., LessiM., Synthesis: International Journal of Methods in Synthetic Organic Chemistry . 2014,第21期

机译：常规芳基化杂种的合成，包括生物活性衍生物，通过钯 - 催化的杂种芳烃与（假）芳基卤化物或芳碘鎓盐的直接C-H芳基化
4. Palladium-catalyzed Selective Arylation of Azulenes at the1,3-Positions based on the C-H Activation by Utilizing 2-PyridylSubstituent as a Directing group [C] . Takuya Nagasawa, Yoshihiro Ogasawara, Tomoaki Yatsu 日本化学会春季年会 . 2020

机译：通过利用2-吡啶基取代剂作为指导基团，基于C-H激活在1,3-位蛋白催化紫红素的选择性浓缩
5. I. Multicatalysis: Development of a Bismuth(III) triflate-catalyzed Nucleophilic addition/ Hydrofunctionalization Reaction in the Synthesis of Complex Heterocycles II. C--H Arylation of Arenes and Heteroarenes with Palladium-Carboxylate Catalysts: Identification of the Catalyst Resting State and the Crucial Role of Pivalate Ligand in Stabilization of the Catalyst III. C--H Arylation of Heteroarenes with Palladium-Carboxylate Catalysts: Importance of Phosphine Ligand for Basic Heteroarene Substrates IV. C--H Arylation of Heteroarenes with Palladium-Carboxylate Catalysts: Effect of the Properties of Basic Heteroarene Substrates on Direct Arylations. [D] . Tundel, Rachel E. 2011

机译：I.多催化作用：在复杂的杂环化合物的合成中三氟甲磺酸铋（III）催化的亲核加成/加氢官能化反应的发展。羰基钯催化剂对芳烃和杂芳烃的CH-H芳基化反应：催化剂静止状态的鉴定以及新戊酸酯配体在稳定催化剂中的关键作用III。羰基钯催化剂催化杂芳烃的CH芳基化：膦配体对基础杂芳烃基质的重要性IV。杂芳烃与钯-羧酸酯的CH芳基化：碱性杂芳烃底物性能对直接芳基化的影响。
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. Inside Cover: Palladium-Catalyzed Zinc-Amide-Mediated CH Arylation of Fluoroarenes and Heteroarenes with Aryl Sulfides (Chem. Eur. J. 42/2015) [O] . Shinya Otsuka, Hideki Yorimitsu, Atsuhiro Osuka 2015

机译：内盖：钯催化的锌 - 酰胺介导的氟芳烃和杂芳烃与芳基硫化物（Chem.EUR.J.20 / 2015）

Palladium-Catalyzed Zinc-Amide-Mediated C-H Arylation of Fluoroarenes and Heteroarenes with Aryl Sulfides

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