A simple and efficient synthesis of 9-arylfluorenes via metal-free reductive coupling of arylboronic acids and N-tosylhydrazones in situ

Shen Xu; Gu Ningning; Liu Ping; Ma Xiaowei; Xie Jianwei; Liu Yan; He Lin; Dai Bin

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A simple and efficient synthesis of 9-arylfluorenes via metal-free reductive coupling of arylboronic acids and N-tosylhydrazones in situ

机译：通过原位的芳基硼酸和N-甲苯胺腙的无金属还原偶联来简单有效地合成9-芳基氟烯酮

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摘要

A general, yet efficient synthesis method of 9-arylfluorenes via metal-free reductive coupling of N-tosylhydrazones and arylboronic acids has been developed. This methodology is realized by a one-pot protocol in two steps involving the preparation of N-tosylhydrazones by reacting tosylhydrazide with 9-fluorenone derivatives, followed by the reductive coupling of arylboronic acid in the presence of potassium carbonate to afford various 9-arylfluorenes analogues in moderate to excellent yields. Importantly, the catalytic system presented here enables the use of easily accessible starting materials and can be employed on a wide variety of substrates with good functional group tolerance. This protocol could also be particularly useful for the synthesis of 9-fluorenyl-substituted carbazolyl compounds.

机译：已经开发了通过无金属无金属肼和芳基硼酸的无金属还原偶联的9-芳基氟烯酮的一般但有效的合成方法。该方法通过单罐方案实现，其中通过使甲苯肼与9-芴酮衍生物反应，然后在碳酸钾存在下进行芳基硼酸的还原偶联，得到碳酸钾的还原偶联以提供各种9-芳基氟烯酮类似物的两步在中度到优异的产量。重要的是，介绍这里的催化系统可以使用易于可接近的原料，并且可以在具有良好官能团耐受性的各种底物上使用。该方案也特别适用于合成9-芴基取代的咔唑基化合物。

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《RSC Advances》 |2015年第78期|共6页
作者
Shen Xu; Gu Ningning; Liu Ping; Ma Xiaowei; Xie Jianwei; Liu Yan; He Lin; Dai Bin;
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Shihezi Univ Xinjiang Bingtuan Key Lab Green Proc Chem Engn Sch Chem &

Chem Engn Shihezi 832003 Peoples R China;

Shihezi Univ Xinjiang Bingtuan Key Lab Green Proc Chem Engn Sch Chem &

Chem Engn Shihezi 832003 Peoples R China;

Shihezi Univ Xinjiang Bingtuan Key Lab Green Proc Chem Engn Sch Chem &

Chem Engn Shihezi 832003 Peoples R China;

Shihezi Univ Xinjiang Bingtuan Key Lab Green Proc Chem Engn Sch Chem &

Chem Engn Shihezi 832003 Peoples R China;

Shihezi Univ Xinjiang Bingtuan Key Lab Green Proc Chem Engn Sch Chem &

Chem Engn Shihezi 832003 Peoples R China;

Shihezi Univ Xinjiang Bingtuan Key Lab Green Proc Chem Engn Sch Chem &

Chem Engn Shihezi 832003 Peoples R China;

Shihezi Univ Xinjiang Bingtuan Key Lab Green Proc Chem Engn Sch Chem &

Chem Engn Shihezi 832003 Peoples R China;

Shihezi Univ Xinjiang Bingtuan Key Lab Green Proc Chem Engn Sch Chem &

Chem Engn Shihezi 832003 Peoples R China;

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1. A simple and efficient synthesis of 9-arylfluorenes via metal-free reductive coupling of arylboronic acids and N-tosylhydrazones in situ [J] . Shen Xu, Gu Ningning, Liu Ping, RSC Advances . 2015,第78期

机译：通过原位的芳基硼酸和N-甲苯胺腙的无金属还原偶联来简单有效地合成9-芳基氟烯酮
2. Synthesis of alpha-arylalkylferrocenes through cesium fluoride-promoted coupling of arylboronic acids with N-tosylhydrazones [J] . Liu Yueqiang, Ma Xiaowei, Liu Yan, Synthetic Communications . 2018,第5a8期

机译：用芳苯肼脱氟化铯促进芳苯甲酸铯的α-芳基烷基二烯酮的合成
3. Synthesis of 3-aryl-1-indanones via CsF-promoted coupling of arylboronic acids with N-tosylhydrazones [J] . Liu Yueqiang, Chen Lingjuan, Liu Yan, Journal of chemical research: reviews and research papers from all branches of chemistry . 2018,第1期

机译：通过CSF促进芳基硼酸与N-甲苯肼肼的偶联合成3-芳基-1-吲哚酮
4. Metal-free Oxidative Coupling of Benzylamines Using Salicylic Acid Derivatives and Its Application to Blue Dye Synthesis [C] . Chun-ping Dong, Shintaro Kodama, Akihiro Nomoto 日本化学会春季年会講演予稿集 . 2018

机译：使用水杨酸衍生物的无金属氧化偶联苄胺及其在蓝染料合成中的应用
5. 1. Reduction of Tertiary Benzamides to Benzaldehydes by an in situ-Generated Schwartz Reagent (Cp2 Zirconium (Hydrogen)Chloride); Formal Synthesis of Lysergic Acid. 2. Ru-Catalyzed Amide-Directed Aryl Carbon-Hydrogen, Carbon-Nitrogen and Carbon-Oxygen Bond Functionalizations: C-B Formation, Carbon-Carbon Suzuki Cross Coupling and Hydrodemethoxylation [D] . Zhao, Yigang 2011

机译：1.通过原位生成的Schwartz试剂（Cp2氯化锆（氢）氯化物）将叔苄酰胺还原为苯甲醛；麦角酸的正式合成。 2. Ru催化的酰胺基芳烃碳氢，碳氮和碳氧键功能化：C-B形成，碳-碳铃木交叉偶联和加氢脱甲氧基化
6. Electron-Poor Fluoro-Containing Arylboronic Acids as Efficient Coupling Partners for Bis(15-cyclooctadiene)nickel(0)/Tricyclohexylphosphine-Catalyzed Cross-Coupling Reactions of Aryl Arenesulfonates [O] . Dr. Wen-Bo Chen, Dr. Chun-Hui Xing, Jie Dong, -1

机译：贫电子含氟的芳基硼酸作为双（15-环辛二烯）镍（0）/三环己基膦催化的芳基芳烃磺酸盐交叉偶联反应的高效偶联剂
7. Correction: Efficient in situ N-heterocyclic carbene palladium(ii) generated from Pd(OAc)2 catalysts for carbonylative Suzuki coupling reactions of arylboronic acids with 2-bromopyridine under inert conditions leading to unsymmetrical arylpyridine ketones: synthesis, characterization and cytotoxic activities [O] . Nedra Touj, Abdullah S. Al-Ayed, Mathieu Sauthier, 2019

机译：校正：从Pd（OAC）2催化剂中产生的芳基氨基酸的2-溴苯酸偶联反应的羰基酸胆碱偶联反应的高效惰性条件，导致非对称芳基吡啶酮：合成，表征和细胞毒性活性

A simple and efficient synthesis of 9-arylfluorenes via metal-free reductive coupling of arylboronic acids and N-tosylhydrazones in situ

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