4-取代的汉斯酯(Hantzsch Esters)作为烷基化试剂参与的有机反应

doi:10.6023/A19050170

化学学报 ›› 2019, Vol. 77 ›› Issue (9): 814-831.DOI: 10.6023/A19050170 上一篇下一篇

所属专题：有机自由基化学

综述

4-取代的汉斯酯(Hantzsch Esters)作为烷基化试剂参与的有机反应

叶盛青^a, 吴劼^a^b^c^*()

^a台州学院医药化工与材料工程学院台州 318000
^b复旦大学化学系上海 200438
^c中国科学院上海有机化学研究所金属有机化学国家重点实验室上海 200032

投稿日期:2019-05-12 发布日期:2019-06-12
通讯作者: 吴劼 E-mail:Jie_wu@fudan.edu.cn
作者简介:叶盛青, 2008年在复旦大学化学系获学士学位; 2013年在复旦大学有机化学专业获理学博士学位(导师: 吴劼教授); 2013年至2015年在美国The Scripps Research Institute从事博士后工作(导师: 余金权教授); 2015年至2019年在苏州诺华制药科技有限公司担任工艺经理; 2019年至今在台州学院医药化工与材料工程学院任副教授. 主要从事类天然产物小分子骨架的有机方法学研究.|吴劼, 1991~1995年就读于江西师范大学化学系, 1995~2000年在中国科学院上海有机化学研究所进行研究生学习(2000年获得博士学位), 2000至2004 年先后在美国哈佛大学(博士后)、洛克菲勒大学艾伦·戴蒙德艾滋病研究中心(访问科学家)及VivoQuest, Inc.(研究员)从事有机合成、药物化学及相关研究工作, 2004年9月回国加入复旦大学化学系(副教授), 2006年4月晋升为教授. 2019年8月加入台州学院医药化工与材料工程学院. 目前主要研究领域: 构建类天然小分子化合物用于抗肿瘤及免疫类疾病、炎症疾病和神经退行性疾病新药研究.
基金资助:
项目受国家自然科学基金资助(Nos.21672037);项目受国家自然科学基金资助(21532001)

4-Substituted Hantzsch Esters as Alkylation Reagents in Organic Synthesis

Ye, Shengqing^a, Wu, Jie^a^b^c^*()

^aSchool of Pharmaceutical and Materials Engineering, Taizhou University, Taizhou 318000, China
^bDepartment of Chemistry, Fudan University, Shanghai 200438, China
^c State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China

Received:2019-05-12 Published:2019-06-12
Contact: Wu, Jie E-mail:Jie_wu@fudan.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China(Nos.21672037);Project supported by the National Natural Science Foundation of China(21532001)

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摘要/Abstract

汉斯酯(Hantzsch Esters)在1881年被合成以来一直被用作还原剂参与加氢还原反应, 近年来科学家发现4-取代的汉斯酯可以发生碳碳键断裂而发生烷基迁移反应. 随后大量以4-取代的汉斯酯类化合物作为烷基化试剂的反应被报道出来, 科学家发现这类烷基化反应的历程主要是烷基自由基的迁移历程. 随着近年自由基化学的快速发展, 为这类新型烷基化试剂的应用发展提供了有力基础. 本文按照该烷基化试剂参与的反应类型分类, 进行简单介绍.

关键词: 4-取代汉斯酯, 1,4-二氢吡啶, 自由基, 烷基化

Hantzsch Esters were first synthesized by Arthur Rudolf Hantzsch in 1881, and widely used in pharmaceutical chemistry. The application of Hantsch Esters in organic synthesis in the early time was mainly focused on the dehydrogenation of 1,4-dihydrogen pyridines (DHPs) in the synthesis of functional pyridines. In 1955, Mauzerall and Westheimer found that Malachite Green could be reduced by Hantzsch Esters to generate the hydrogenated product. Then these DHPs were extensively used as a reductant for decades due to their electron and hydrogen donating properties. In recent years, scientist found that C—C bond cleavage at 4-position of 4-substituted Hantzsch Esters would lead alkyl transfer, and the alkylation process was a radical process. With the rapid development of free radical chemistry, various alkylation reactions using 4-substituted Hantzsch Esters as alkylation reagent have been developed, such as addition reactions of imines and alkenes; cross-coupling reactions with aryl halides; substitution reactions with functional aromatics; Tsuji-Trost reaction; radical insertion with sulfur dioxide; and asymmetric alkylation etc. The advantages in alkylation transfer by using 4-substituted Hantzsch Esters as alkyl source in the past five years were witnessed dramatically: (1) Highly toxic alkyl metal reagents could be avoided in the alkylation reactions; (2) Compared with the moisture sensitivity of alkyl metal reagents Hantzsch Esters are easily handling; (3) 1,4-Dihydrogen pyridines (DHPs) are biologically-inspired model molecular of reduced nicotinamide adenine dinucleotide (NADH), which would expand the application in biosynthesis. A brief summary in this field is presented in this review, and the advances are classified according to different reaction types. Although these creativity works were developed, there are still some challenges: (1) Could aromatic groups at 4-position of 4-substituted Hantzsch Esters serve as arylation reagents? (2) How to recover the rest pyridine part of Hantzsch Esters after alkylation; (3) New type reactions need to be developed for the asymmetric synthesis.

Key words: 4-substituted Hantzsch Ester, 1,4-dihydropyridine, free radical, alkylation

引用此文

叶盛青, 吴劼. 4-取代的汉斯酯(Hantzsch Esters)作为烷基化试剂参与的有机反应[J]. 化学学报, 2019, 77(9): 814-831.

Ye, Shengqing, Wu, Jie. 4-Substituted Hantzsch Esters as Alkylation Reagents in Organic Synthesis[J]. Acta Chimica Sinica, 2019, 77(9): 814-831.

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图/表 31

图式1. 1,4-二氢吡啶4-位的氢或烷基迁移

Scheme 1. Hydrongen and alkyl transfer of DHPs

图式2. 路易斯酸催化的烷基对亚胺的加成反应

Scheme 2. Lewis acid catalyzed alkylation of imine

图式3. 光催化的烷基自由基对亚胺的加成

Scheme 3. Radical alkylation of imines catalyzed by photocatalyst

图式4. 光催化烷基自由基对烯烃的加成

Scheme 4. Radical alkylation of olefins catalyzed by photocatalyst

图式5. 有机光敏催化剂催化的烷基自由基对烯烃的加成

Scheme 5. Alkylation of olefins catalyzed by organo-photocatalyst

图式6. 路易斯酸和有机光敏催化剂共催化的烷基自由基对烯烃的加成

Scheme 6. Alkylation of olefins co-catalyzed by Lewis acid and organo-photocatalyst

图式7. 通过光直接激发1,4-二氢吡啶产生烷基自由基

Scheme 7. Generation of alkyl radicals from direct excitation of DHPs

图式8. 自由基加成/负离子环化反应

Scheme 8. Radical/polar annulation reactions

图式9. 烷基自由基对三氟甲基取代烯烃的脱氟烷基化反应

Scheme 9. Defluorinative alkylation of 1-trifluoromethyl alkenes with alkyl radicals

图式10. sp3碳卤键断裂的烷基化偶联反应

Scheme 10. Alkylation of alkyl bromide compounds

图式11. sp2碳卤键断裂的烷基化偶联反应

Scheme 11. Alkylation of aryl halides

图式12. 光敏催化剂与过渡金属Ni共催化的sp2碳卤键断裂的烷基化偶联反应

Scheme 12. Photoredox/Nickel co-catalyzed alkylation of aryl halides

图式13. 通过光敏催化剂与过渡金属Ni共催化来合成芳基取代的糖类化合物

Scheme 13. Synthesis of arylated saccharides through Nickel and Photoredox dual catalysis

图式14. 通过光敏催化剂与过渡金属Ni共催化来合成羰基取代的糖类化合物

Scheme 14. Synthesis of acylated saccharides through Nickel and Photoredox dual catalysis

图式15. 通过光敏催化剂与过渡金属Ni共催化的卤代烯烃的烷基化偶联反应

Scheme 15. Cross-coupling of alkenyl halides through Nickel and Photoredox dual catalysis

图式16. 过渡金属Ni参与的芳基溴代物的烷基化偶联反应

Scheme 16. Cross-coupling of aryl bromide through Nickel catalysis

图式17. 烷基自由基的炔基化反应

Scheme 17. Alkynylation with alkyl radicals

图式18. 光促进的烷基自由基的炔基化反应

Scheme 18. Visible light promoted alkynylation with alkyl radicals

图式19. 硝基烯烃的硝基取代反应

Scheme 19. Replacing the nitro group of nitro-olefins

图式20. 烷基自由基对芳环上氰基的取代反应

Scheme 20. Aromatic substitution reactions of cyanoarenes with alkyl radicals

图式21. 烷基自由基对杂环芳基砜类化合物取代反应

Scheme 21. Desulfonative alkylation of N-heteroaryl sulfones

图式22. η6-芳基取代的羰基锰化合物的碳氢烷基化反应

Scheme 22. Alkylation of (η6-arene)tricarbonylmanganese complexes

图式23. 烷基自由基对氮杂环的碳氢键取代反应

Scheme 23. Alkylation of N-heteroaryl complexes

图式24. 烷基自由基参与的单电子Tsuji-Trost反应

Scheme 24. Single-electron Tsuji-Trost reaction with alkyl radicals

图式25. 烷基自由基对二氧化硫的插入反应

Scheme 25. Insertion of sulfur dioxide with alkyl radicals

图式26. 烷基自由基对二氧化硫和贫电子烯烃的插入反应

Scheme 26. Insertion of sulfur dioxide and electron-deficient alkenes with alkyl readicals

图式27. 烷基自由基对丙烯醛的不对称加成

Scheme 27. Stereoselective addition of enals with alkyl radicals

图式28. 酰基自由基对丙烯醛的不对称加成

Scheme 28. Stereoselective addition of enals with acyl radicals

图式29. 手性光敏催化剂催化的烷基自由基对贫电子烯烃的手性加成

Scheme 29. Enantioselective β-alkylation electron-deficient alkenes catalyzed by chiral photoredox catalyst

图式30. 烯丙基的不对称烷基化反应

Scheme 30. Enantioselective allylic alkylation

图式31. 碳氧双键的不对称加成

Scheme 31. Enantioselective alkylation of C=O bond

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4-取代的汉斯酯(Hantzsch Esters)作为烷基化试剂参与的有机反应

4-Substituted Hantzsch Esters as Alkylation Reagents in Organic Synthesis

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