Single-Electron-Transfer (SET)-Induced Oxidative Biaryl Coupling by Polyalkoxybenzene-Derived Diaryliodonium(III) Salts

Nobutaka Yamaoka; Kohei Sumida; Itsuki Itani; Hiroko Kubo; Yusuke Ohnishi; Sho Sekiguchi; Toshifumi Dohi; Yasuyuki Kita

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Single-Electron-Transfer (SET)-Induced Oxidative Biaryl Coupling by Polyalkoxybenzene-Derived Diaryliodonium(III) Salts

机译：聚烷氧基苯衍生的二芳基碘鎓盐在单电子转移（SET）诱导的氧化联芳基偶联中的作用

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摘要

Metal-free oxidative C-C coupling by using polyalkoxybenzenederived diaryliodonium(III) salts as both the oxidant and aryl source has been developed. These salts can induce single-electron-transfer (SET) oxidation to yield electron-rich arenes and subsequently transfer the polyalkoxyphenyl group into in situ generated aromatic radical cations to produce biaryl products. The reaction is promoted by a Lewis acid that activates the iodonium salts. It has been revealed that the reactivity of the salts under acidic conditions is quite different to their known behavior under basic conditions. The reactivity preference of a series of iodonium salts in the SET oxidation and their ligand transfer abilities have been systematically investigated and the results are summarized in this report.

机译：通过使用聚烷氧基苯衍生的二芳基碘鎓（III）盐作为氧化剂和芳基源，开发了无金属的氧化C-C偶联。这些盐可诱导单电子转移（SET）氧化，生成富电子芳烃，随后将聚烷氧基苯基基团转移到原位生成的芳族自由基阳离子中，从而生成联芳基产物。该反应通过激活碘鎓盐的路易斯酸来促进。已经发现，盐在酸性条件下的反应性与它们在碱性条件下的已知行为完全不同。系统研究了一系列碘盐在SET氧化中的反应性偏好及其配体转移能力，本报告总结了结果。

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《Chemistry: A European journal》 |2013年第44期|共8页
作者
Nobutaka Yamaoka; Kohei Sumida; Itsuki Itani; Hiroko Kubo; Yusuke Ohnishi; Sho Sekiguchi; Toshifumi Dohi; Yasuyuki Kita;
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正文语种 eng
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关键词
biaryls; cross coupling; hypervalent compound; iodine; radical ions; umpolung;

机译：联芳基;交叉偶联;高价化合物;碘;自由基离子;蛋白;

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1. Single-Electron-Transfer (SET)-Induced Oxidative Biaryl Coupling by Polyalkoxybenzene-Derived Diaryliodonium(III) Salts [J] . Nobutaka Yamaoka, Kohei Sumida, Itsuki Itani, Chemistry: A European journal . 2013,第44期

机译：聚烷氧基苯衍生的二芳基碘鎓盐在单电子转移（SET）诱导的氧化联芳基偶联中的作用
2. Oxidative Cross-Coupling of Arenes Induced by Single-Electron Transfer Leading to Biaryls by Use of Organoiodine(III) Oxidants [J] . Toshifumi Dohi, Motoki Ito, Koii Morimoto Angewandte Chemie . 2008,第7期

机译：单电子转移导致的芳烃的氧化交叉偶联导致使用有机碘（III）氧化剂
3. The synthesis of head-to-tail (H-T) dimers of 3-substituted thiophenes by the hypervalent iodine(III)-induced oxidative biaryl coupling reaction [J] . Toshifumi Dohi, Koji Morimoto, Yorito Kiyono, Chemical Communications . 2005,第23期

机译：高价碘（III）诱导的氧化联芳基偶联反应合成3-取代噻吩的头对尾（H-T）二聚体
4. Development and Mechanistic Study of Bifunctional Phosphonium Salt-Catalyzed Coupling Reactions of Carbon Dioxide with Epoxides [C] . Yasunori Toda, Yutaka Komiyama, Hiroyoshi Esaki 日本化学会春季年会講演予稿集 . 2018

机译：环氧化物二氧化碳双官能鏻盐催化偶联反应的发展与机械研究
5. I. Heterogeneous cross-coupling reactions catalyzed by nickel-in-charcoal and copper-in-charcoal. II. Asymmetric 1,2/1,4-reductions catalyzed by copper hydride. III. Atropselective synthesis of the biaryl A-B ring system of vancomycin utilizing an internally tethered, nonracemic ligand. [D] . Lee, Ching-Tien. 2009

机译：I.炭中镍和炭中铜催化的非均相交叉偶联反应。二。氢化铜催化的不对称1,2 / 1,4-还原反应。三，利用内部束缚的非外消旋配体进行万古霉素联芳基A-B环系统的选择性催化合成。
6. SET-Induced Biaryl Cross-Coupling:An SRN1 Reaction [O] . BrandonE. Haines, Olaf Wiest, * -1

机译：SET诱导的联芳基交叉偶联：SRN1反应
7. Development of Novel Aryl Coupling Reaction Based on the Single-Electron-Transfer (SET) Oxidation Ability of Iodonium Salts [O] . 山岡信貴 2014

机译：基于碘盐单电子转移（SET）氧化能力的新型芳基偶联反应的研究

Single-Electron-Transfer (SET)-Induced Oxidative Biaryl Coupling by Polyalkoxybenzene-Derived Diaryliodonium(III) Salts

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