可见光催化的硫醚选择性氧化和自由基加成反应研究
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摘要
可见光催化的有机合成反应是通过光催化剂媒介利用太阳光来激活反应物发生化学反应，是目前有机化学一个新兴领域，其发展在国际上还处于起步阶段。直接利用太阳光中可见光部分促进化学合成反应的研究很少，因此光化学有机合成反应的研究很有意义，该领域的研究不仅可以发现新的化学反应，而且有其现实和潜在的重大应用价值。
本论文研究的主要内容是通过研究可见光催化的有机合成反应，利用可见光化学，我们发展了可见光催化的硫醚选择性氧化，首次报道了可见光催化的原子转移自由基环加成反应等，丰富了可见光催化的反应化学，拓展了可见光催化体系的应用范围。
本文主要分为五个部分：
第一章，可见光催化无金属的需氧的硫醚选择性氧化。主要研究了在可见光条件下以空气中的氧气为氧化剂，以Rose Bengal为光敏剂，高选择性地将硫醚氧化为亚砜，反应条件温和，操作简便，是一个非常绿色的反应体系。
第二章，可见光催化的分子间的原子转移环化（ATRC）反应。碘甲基环丙烷衍生物在可见光催化下三元环开环生成高烯丙基自由基中间体，该中间体和不饱和双键、三键发生[3+2]环加成反应并成功实现了碘原子的转移。由简单原料出发合成了多种取代基的环戊烷衍生物，丰富了可见光催化的反应化学。
第三章，可见光催化的分子内原子转移环化（ATRC）反应。在分子间反应研究的基础上，我们成功的发展了一种可见光催化的Ueno-Stork反应。该光致氧化还原反应以烷基碘做为自由基前体，成功构建了多种并环四氢呋喃骨架。该方法可以用于构建哌啶并四氢呋喃环、吡啶并四氢呋喃环、环己烷并四氢呋喃环、环戊烷并四氢呋喃环等丰富的骨架类型，为其在复杂结构化合物的合成应用提供了可能。
第四章，我们实现了在可见光催化条件下的Heck-type反应，在tBuOK存在条件下，不需要添加光敏剂，专一的生成热力学稳定的反式产物。而在加入光敏剂后，反应选择性地生成顺式为主的产物。实现了对化学选择性的较好控制。
第五章可见光催化的二甲基苯胺自由基对马来酰亚胺自由基环加成反应。N原子位烷基自由基作为一类活泼的富电子自由基中间体，显示出了对缺电子的马来酰亚胺双键良好的加成性能。加成后产生的自由基中间体进一步对苯环进行加成，生成取代的喹啉衍生物。
Reactions triggered by light are unique synthetic methods to chemists.Photoinduced redox processes using visible light in conjunction with sensitizers offera great variety of useful catalytic transformations in the realm of organic synthesis.
The recent literature reports have shown that this field is expanding substantially.Visible-light-promoted reaction becomes an important area in new organic reactionsdevelopment. This thesis research work focuses on the development of visible lightpromoted new synthetically useful methodolodies. We have developed a simplemetal-free catalytic sulfoxidation under visible light and air, and four photoredoxradical addition/substituation reactions, including intermolecular visible-lightphotoredox atom-transfer radical [3+2] cyclization of2-(iodomethyl)cyclopropane-1,1-dicarboxylate with alkenes and alkynes; visible lightphotoredox atom transfer Ueno-Stork reaction, a stereo-selective “Heck-type”reaction and a visible-light-mediated free radical [4+2] cycloaddition reaction ofdimethyl aniline to maleimide derivatives. These new reactions are good additions tothe field of visible-light photoredox chemistry.
This thesis is divided into five parts:
Chapter1: A simple metal-free catalytic sulfoxidation under visible light and air.A metal-free aerobic selective sulfoxidation photosensitized by Rose Bengal orsolid-supported Rose Bengal has been developed. The reaction utilizes visible light asthe driving force and molecular oxygen as the oxidant. The method is practical for itshigh efficiency and selectivity, extremely simple workup procedure, and minimalwaste generation.
Chapter2: An intermolecular visible-light photoredox [3+2] ATRC reaction wasdeveloped. In this reaction, cyclopentane/cyclopentene derivatives were formed fromtwo structurally simple molecules through the construction of two new C-C bonds. Inour study, it was found that the homoallylic malonate radical was reactive towards electron-rich alkenes. But the reactions with unactivated alkenes were sluggish.Zn(OAc)2was found to enhance the reactivity of the radical intermidiate. The use ofLewis acid expanded the scope of the alkene substrates of the reaction. Comparedwith existing methods, the procedure is operationally simpler and does not involve theuse of stoichiometric hazardous radical initiators.
Chapter3: A visible light-promoted atom transfer Ueno–Stork reaction wasdeveloped using Ir(ppy)2(dtb-bpy)PF6as the sensitizer.2-Iodoethyl propargyl ethersor2-iodoethyl allyl ethers were used as the radical precursors to constructtetrahydrofuran-containing fused [6,5] and [5,5] bicyclic frameworks.
Chapter4: We developed a Heck-type reaction under visible light irraditon. Inthe absent of photosensitizer, only the thermodynamically more stable E-olefin wasformed as the only product. With photosensitizer the reaction generates Z-olefin asthe major product.
Chapter5: Visible-light-mediated free radical addition reaction of dimethylaniline to maleimide derivatives.-Amino alkyl radical, an electronic-rich radical,showed high reactivity toward electron-deficient double bond of maleimids. Followedby free radical addition to benzene ring, quinoline derivatives was formed efficiently.
本论文研究的主要内容是通过研究可见光催化的有机合成反应，利用可见光化学，我们发展了可见光催化的硫醚选择性氧化，首次报道了可见光催化的原子转移自由基环加成反应等，丰富了可见光催化的反应化学，拓展了可见光催化体系的应用范围。
本文主要分为五个部分：
第一章，可见光催化无金属的需氧的硫醚选择性氧化。主要研究了在可见光条件下以空气中的氧气为氧化剂，以Rose Bengal为光敏剂，高选择性地将硫醚氧化为亚砜，反应条件温和，操作简便，是一个非常绿色的反应体系。
第二章，可见光催化的分子间的原子转移环化（ATRC）反应。碘甲基环丙烷衍生物在可见光催化下三元环开环生成高烯丙基自由基中间体，该中间体和不饱和双键、三键发生[3+2]环加成反应并成功实现了碘原子的转移。由简单原料出发合成了多种取代基的环戊烷衍生物，丰富了可见光催化的反应化学。
第三章，可见光催化的分子内原子转移环化（ATRC）反应。在分子间反应研究的基础上，我们成功的发展了一种可见光催化的Ueno-Stork反应。该光致氧化还原反应以烷基碘做为自由基前体，成功构建了多种并环四氢呋喃骨架。该方法可以用于构建哌啶并四氢呋喃环、吡啶并四氢呋喃环、环己烷并四氢呋喃环、环戊烷并四氢呋喃环等丰富的骨架类型，为其在复杂结构化合物的合成应用提供了可能。
第四章，我们实现了在可见光催化条件下的Heck-type反应，在tBuOK存在条件下，不需要添加光敏剂，专一的生成热力学稳定的反式产物。而在加入光敏剂后，反应选择性地生成顺式为主的产物。实现了对化学选择性的较好控制。
第五章可见光催化的二甲基苯胺自由基对马来酰亚胺自由基环加成反应。N原子位烷基自由基作为一类活泼的富电子自由基中间体，显示出了对缺电子的马来酰亚胺双键良好的加成性能。加成后产生的自由基中间体进一步对苯环进行加成，生成取代的喹啉衍生物。
Reactions triggered by light are unique synthetic methods to chemists.Photoinduced redox processes using visible light in conjunction with sensitizers offera great variety of useful catalytic transformations in the realm of organic synthesis.
The recent literature reports have shown that this field is expanding substantially.Visible-light-promoted reaction becomes an important area in new organic reactionsdevelopment. This thesis research work focuses on the development of visible lightpromoted new synthetically useful methodolodies. We have developed a simplemetal-free catalytic sulfoxidation under visible light and air, and four photoredoxradical addition/substituation reactions, including intermolecular visible-lightphotoredox atom-transfer radical [3+2] cyclization of2-(iodomethyl)cyclopropane-1,1-dicarboxylate with alkenes and alkynes; visible lightphotoredox atom transfer Ueno-Stork reaction, a stereo-selective “Heck-type”reaction and a visible-light-mediated free radical [4+2] cycloaddition reaction ofdimethyl aniline to maleimide derivatives. These new reactions are good additions tothe field of visible-light photoredox chemistry.
This thesis is divided into five parts:
Chapter1: A simple metal-free catalytic sulfoxidation under visible light and air.A metal-free aerobic selective sulfoxidation photosensitized by Rose Bengal orsolid-supported Rose Bengal has been developed. The reaction utilizes visible light asthe driving force and molecular oxygen as the oxidant. The method is practical for itshigh efficiency and selectivity, extremely simple workup procedure, and minimalwaste generation.
Chapter2: An intermolecular visible-light photoredox [3+2] ATRC reaction wasdeveloped. In this reaction, cyclopentane/cyclopentene derivatives were formed fromtwo structurally simple molecules through the construction of two new C-C bonds. Inour study, it was found that the homoallylic malonate radical was reactive towards electron-rich alkenes. But the reactions with unactivated alkenes were sluggish.Zn(OAc)2was found to enhance the reactivity of the radical intermidiate. The use ofLewis acid expanded the scope of the alkene substrates of the reaction. Comparedwith existing methods, the procedure is operationally simpler and does not involve theuse of stoichiometric hazardous radical initiators.
Chapter3: A visible light-promoted atom transfer Ueno–Stork reaction wasdeveloped using Ir(ppy)2(dtb-bpy)PF6as the sensitizer.2-Iodoethyl propargyl ethersor2-iodoethyl allyl ethers were used as the radical precursors to constructtetrahydrofuran-containing fused [6,5] and [5,5] bicyclic frameworks.
Chapter4: We developed a Heck-type reaction under visible light irraditon. Inthe absent of photosensitizer, only the thermodynamically more stable E-olefin wasformed as the only product. With photosensitizer the reaction generates Z-olefin asthe major product.
Chapter5: Visible-light-mediated free radical addition reaction of dimethylaniline to maleimide derivatives.-Amino alkyl radical, an electronic-rich radical,showed high reactivity toward electron-deficient double bond of maleimids. Followedby free radical addition to benzene ring, quinoline derivatives was formed efficiently.
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