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Transition-Metal Catalyzed sp3-C--H Bond Amination from Aryl Azides.

機(jī)譯：芳基疊氮化物的過(guò)渡金屬催化sp3-C-H鍵胺化。

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摘要

This thesis studied transition metal catalyzed sp3-C-H amination reaction using aryl azides as the nitrogen source to produce N-heterocyclic compounds including indole and indoline. First, Rh2(esp)2 mediated aliphatic C-H bond amination reactions of aryl azides without requiring a strong electron-withdrawing group on the nitrogen atom was presented. The mechanistic study carried out on the reactivity of stereospecific labeled aryl azides supported for the formation of the nitrenoid followed by stepwise pathway with the syn-C-H bond through radical species. Second, the tandem ethereal C-H bond amination-elimination-[1,2]-migration reaction catalyzed by inexpensive, nontoxic FeBr2 was discussed. With the successful isolation of some intermediates, mechanistic experiments revealed FeBr2to be essential for both the C-H bond amination as well as the iminium ion generation. Finally, dirhodium(II) carboxylate promoting the formation of 1,2,3-trisubstituted indoles from styryl azides was investigated. The proposed mechanism involved 4p-electron-5-atom electrocyclization and formation of spirocyclic cation that triggers the migration process.
機(jī)譯：本文研究了以芳基疊氮化物為氮源的過(guò)渡金屬催化的sp3-C-H胺化反應(yīng)，制備了包括吲哚和二氫吲哚在內(nèi)的N-雜環(huán)化合物。首先，提出了Rh2（esp）2介導(dǎo)的芳基疊氮化物的脂肪族C-H鍵胺化反應(yīng)，該反應(yīng)不需要氮原子上具有強(qiáng)吸電子基團(tuán)。對(duì)立體特異性標(biāo)記的芳基疊氮化物的反應(yīng)性進(jìn)行了機(jī)理研究，該疊氮物支持形成亞硝基化合物，然后通過(guò)自由基物質(zhì)通過(guò)syn-C-H鍵逐步進(jìn)行。其次，討論了由廉價(jià)，無(wú)毒的FeBr2催化的串聯(lián)醚式C-H鍵胺化-消除[1,2]遷移反應(yīng)。隨著一些中間體的成功分離，機(jī)理實(shí)驗(yàn)表明，F(xiàn)eBr2對(duì)于C-H鍵胺化和亞胺離子生成都是必不可少的。最后，研究了能促進(jìn)苯乙烯疊氮化物形成1,2,3-三取代吲哚的羧酸二（II）羧酸鹽。擬議的機(jī)制涉及4p電子5原子電環(huán)化和螺環(huán)陽(yáng)離子的形成，從而觸發(fā)遷移過(guò)程。

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  • 作者

    Nguyen, Quyen.;

  • 作者單位

    University of Illinois at Chicago.;

  • 授予單位 University of Illinois at Chicago.;
  • 學(xué)科 Organic chemistry.
  • 學(xué)位 Ph.D.
  • 年度 2014
  • 頁(yè)碼 327 p.
  • 總頁(yè)數(shù) 327
  • 原文格式 PDF
  • 正文語(yǔ)種 eng
  • 中圖分類 遙感技術(shù);
  • 關(guān)鍵詞

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