过渡金属催化的脱羧反应及相转移催化剂催化的环化反应研究
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摘要
第一章：
在第一章中,系统地概括了各类脱羧反应的发展和在有机合成中的应用。主要包括脱羧质子化反应、脱羧自聚反应、脱羧偶联反应、脱羧-C/H活化反应、脱羧烯丙基化反应、脱羧苄基化反应、脱羧环化反应以及脱羧的其他反应。
第二章：
我们首次通过脱羧的方法成功地构筑了在生物体内有重要作用的碳-磷键(Csp3-P,Csp2-P and Csp-P).和传统的C-P的构筑相比,该反应具有操作简单,反应温和,产物单一,选择性好等特点,利用该反应,我们可以很顺利地得到一些关于含磷的配体。通过X-Ray单晶衍射确定了产物的结构,并且提出了催化循环的机理假设。
第三章：
我们介绍了在钯/碳催化的体系下使用炔丙基化合物合成含有末端双键的苯并呋喃衍生物以及含有丙二烯官能团的苯并呋喃衍生物。反应操作简单易行,不需要在惰气的氛围中便可进行,并且使用了非常少的催化剂。该反应的另一个特点是通过C-C的形成构筑苯并呋喃的衍生物的方法还是比较少见的。
第四章：
我们首次用相转移催化剂来催化分子内的环化反应形成具有生物活性非常重要的二取代苯并呋喃衍生物,该反应条件温和,操作简单,产率很高,催化剂廉价易得,环境友好,底物的适用性强,另外用我们的体系还可以环化茚的衍生物。
第五章：
我们通过相转移催化实现了分子内的亲芳氧化和亲胺化反应得到了单取代和二取代的苯并呋喃以及异吲哚啉-1-酮的衍生物,而且对于以前报道过的用过渡金属催化的炔丙基碳酸酯的环化反应,我们的体系依然适用。总体来说,反应条件温和,操作简单,产率较高,催化剂环境友好,廉价易得。
第六章：
我们成功地实现了用相转移催化剂来促进两分子的反应,该反应通过两个迈克尔加成得到多取代的4H-吡喃的衍生物。反应条件温和而且具有100%的原子经济性。
Chapter 1.
The development and application of decarboxylation reactions in organic synthesis were summarized in detail, which includes decarboxylative protonation reaction, decarboxylative homocoupling reaction, decarboxylative coupling reaction, decarboxylative-C/H activation reaction, decarboxylative alkylation reaction, decarboxylative cyclization and other types of decarboxylation reaction.
Chapter 2.
This work is the first example of decarboxylative coupling to construct C-P bond(Csp3-P, Csp2-P and Csp-P), which is highly important in biologically active products. Compared with traditional methods, the reaction affords simple operation, easily availability, mild reaction condition, the best regioselective and chemoselective, good functional group tolerance. The reaction is applied to synthesize various phosphorus ligand and a possible mechansim is proposed. The structure was definitively secured by an X-ray crystal structure analysis.
Chapter 3.
A novel Pd/C-catalyzed reaction for the synthesis of benzo[b]furan derivatives including terminal olefins or allenyl group from propargylic compounds with high regioselectivity was described in detail. This reaction was easily conducted under ambient conditions of air and lower catalyst loading was used in this process. In particular, there have been few reports on benzo[b]furans syntheses from alkynylbenzene derivations via carbon-carbon bond (C-C) cyclization.
Chapter 4.
A variety of substituted benzo[b]furans are readily prepared in good to excellent yields under the mild reaction conditions with PTC (Phase-transfer catalysis) for the first time. This methodology accommodates simple experimental operations, inexpensive and environmentally benign catalyst, metal catalyst-free condition, facile reagents and possibility to conduct large-scale preparations. Furthermore, the indane derivatives were also smoothly proceeded in our system.
Chapter 5.
Phase-transfer-catalyzed intramolecular cyclization reaction of forming benzo[b]furan and 3-methyleneisoindoline-1-one derivatives has been developed. The cyclization reaction of propargylic carbonates was also described under metal-free condition and the reaction was reported by Pd and Ni before. The catalysts are cheap and environmentally friendly and the substrates are readily available and the procedure is simple, rapid, and general.
Chapter 6.
A variety of substituted 4H-pyrans are readily prepared in moderate to good yields under the mild reaction conditions by nucleophilic addition to electron-deficient 1,3-conjugated enynes with PTC (Phase-transfer catalysis). The reaction is mild and easily conducted and 100% atom-economic.
在第一章中,系统地概括了各类脱羧反应的发展和在有机合成中的应用。主要包括脱羧质子化反应、脱羧自聚反应、脱羧偶联反应、脱羧-C/H活化反应、脱羧烯丙基化反应、脱羧苄基化反应、脱羧环化反应以及脱羧的其他反应。
第二章：
我们首次通过脱羧的方法成功地构筑了在生物体内有重要作用的碳-磷键(Csp3-P,Csp2-P and Csp-P).和传统的C-P的构筑相比,该反应具有操作简单,反应温和,产物单一,选择性好等特点,利用该反应,我们可以很顺利地得到一些关于含磷的配体。通过X-Ray单晶衍射确定了产物的结构,并且提出了催化循环的机理假设。
第三章：
我们介绍了在钯/碳催化的体系下使用炔丙基化合物合成含有末端双键的苯并呋喃衍生物以及含有丙二烯官能团的苯并呋喃衍生物。反应操作简单易行,不需要在惰气的氛围中便可进行,并且使用了非常少的催化剂。该反应的另一个特点是通过C-C的形成构筑苯并呋喃的衍生物的方法还是比较少见的。
第四章：
我们首次用相转移催化剂来催化分子内的环化反应形成具有生物活性非常重要的二取代苯并呋喃衍生物,该反应条件温和,操作简单,产率很高,催化剂廉价易得,环境友好,底物的适用性强,另外用我们的体系还可以环化茚的衍生物。
第五章：
我们通过相转移催化实现了分子内的亲芳氧化和亲胺化反应得到了单取代和二取代的苯并呋喃以及异吲哚啉-1-酮的衍生物,而且对于以前报道过的用过渡金属催化的炔丙基碳酸酯的环化反应,我们的体系依然适用。总体来说,反应条件温和,操作简单,产率较高,催化剂环境友好,廉价易得。
第六章：
我们成功地实现了用相转移催化剂来促进两分子的反应,该反应通过两个迈克尔加成得到多取代的4H-吡喃的衍生物。反应条件温和而且具有100%的原子经济性。
Chapter 1.
The development and application of decarboxylation reactions in organic synthesis were summarized in detail, which includes decarboxylative protonation reaction, decarboxylative homocoupling reaction, decarboxylative coupling reaction, decarboxylative-C/H activation reaction, decarboxylative alkylation reaction, decarboxylative cyclization and other types of decarboxylation reaction.
Chapter 2.
This work is the first example of decarboxylative coupling to construct C-P bond(Csp3-P, Csp2-P and Csp-P), which is highly important in biologically active products. Compared with traditional methods, the reaction affords simple operation, easily availability, mild reaction condition, the best regioselective and chemoselective, good functional group tolerance. The reaction is applied to synthesize various phosphorus ligand and a possible mechansim is proposed. The structure was definitively secured by an X-ray crystal structure analysis.
Chapter 3.
A novel Pd/C-catalyzed reaction for the synthesis of benzo[b]furan derivatives including terminal olefins or allenyl group from propargylic compounds with high regioselectivity was described in detail. This reaction was easily conducted under ambient conditions of air and lower catalyst loading was used in this process. In particular, there have been few reports on benzo[b]furans syntheses from alkynylbenzene derivations via carbon-carbon bond (C-C) cyclization.
Chapter 4.
A variety of substituted benzo[b]furans are readily prepared in good to excellent yields under the mild reaction conditions with PTC (Phase-transfer catalysis) for the first time. This methodology accommodates simple experimental operations, inexpensive and environmentally benign catalyst, metal catalyst-free condition, facile reagents and possibility to conduct large-scale preparations. Furthermore, the indane derivatives were also smoothly proceeded in our system.
Chapter 5.
Phase-transfer-catalyzed intramolecular cyclization reaction of forming benzo[b]furan and 3-methyleneisoindoline-1-one derivatives has been developed. The cyclization reaction of propargylic carbonates was also described under metal-free condition and the reaction was reported by Pd and Ni before. The catalysts are cheap and environmentally friendly and the substrates are readily available and the procedure is simple, rapid, and general.
Chapter 6.
A variety of substituted 4H-pyrans are readily prepared in moderate to good yields under the mild reaction conditions by nucleophilic addition to electron-deficient 1,3-conjugated enynes with PTC (Phase-transfer catalysis). The reaction is mild and easily conducted and 100% atom-economic.
引文
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