苯炔参与的去芳构化反应研究进展

doi:10.6023/cjoc202009009

摘要/Abstract

去芳构化反应是有机化学热点研究领域之一, 可从二维平面分子出发构筑高官能团化的三维立体分子. 近年来, 苯炔作为一类高活性中间体被有机化学家们广泛用于去芳构化反应研究中, 并取得了一系列创新成果. 从含氮芳杂环同苯炔的去芳构化反应、苯炔与双烯体的[4+2]环加成去芳构化反应以及苯炔以其它途径参与的去芳构化反应三个方面, 对机理进行系统性综述, 并对该类反应未来的发展方向予以展望.

关键词: 去芳构化, 苯炔, 含氮杂环, 多组分反应, 环加成反应

Dearomatization reaction is one of the most popular research areas in organic chemistry. It could build highly functionalized three-dimensional molecules from readily available planar aromatic compounds. In recent years, arynes as reactive intermediates have been extensively investigated in dearomatization reactions, and a series of synthetic protocols have been reported. The mechanisms of the dearomatization reaction of azaarenes with arynes, the [4+2] cycloaddition dearomatization reactions of arynes with dienes, and the dearomatization of arynes in other pathways are reviewed. The insights and outlooks regarding this rapid developing field are also provided.

Key words: dearomatization reactions, aryne, N-heteroaromatics, multicomponent reaction, cycloaddition reaction

引用此文

闫强, 范荣, 刘斌斌, 苏帅松, 王勃, 姚团利, 谭嘉靖. 苯炔参与的去芳构化反应研究进展[J]. 有机化学, 2021, 41(2): 455-470.

Qiang Yan, Rong Fan, Binbin Liu, Shuaisong Su, Bo Wang, Tuanli Yao, Jiajing Tan. Recent Progress in Aryne Participated Dearomatization Reactions[J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 455-470.

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图/表 30

图式1. 苯炔、乙腈与异喹啉的三组分去芳构化反应

Scheme 1. Three-component dearomatization reaction of arynes, acetonitriles and isoquinolines

图式2. 苯炔、端炔(酮)和喹啉的三组分去芳构化反应

Scheme 2. Three-component dearomatization reaction of arynes, terminal alkynes (ketones) and quinolines

图式3. 苯炔引发的亚磷酸二酯与(异)喹啉的三组分去芳构化反应

Scheme 3. Aryne induced three-component dearomatization reaction of dialkylphosphites and (iso)quinolines

图式4. 苯炔引发的(异)喹啉与氯仿的三组分去芳构化反应

Scheme 4. Aryne induced three-component dearomatization reaction of (iso)quinolines and chloroform

图式5. 苯炔、靛红与喹啉(吡啶)的三组分反应

Scheme 5. Three-component reaction of arynes, isatins and quinolines (pyridines)

图式6. 苯炔、醛(酮)与喹啉的三组分去芳构化反应

Scheme 6. Three-component dearomatization reaction of arynes, aldehydes(ketones) and quinolines

图式7. 苯炔引发的醛(酮)与喹啉的三组分去芳构化反应

Scheme 7. Aryne induced dearomatization reaction of aldehydes (ketones) and quinolines

图式8. 苯炔、四氯化碳与氮杂芳烃的三组分去芳构化反应

Scheme 8. Three-component dearomatization reaction of arynes, carbon tetrachloride and azaarenes

图式9. 苯炔与2-吡啶羧酸酯的去芳构化反应

Scheme 9. Dearomatization reaction of arynes and pyridin-2-yl carboxylates

图式10. 苯炔与2-丙烯酸酯基吡啶以及2-亚胺基吡啶的去芳构化反应

Scheme 10. Dearomatization reaction of arynes with 2-acrylate pyridines or 2-iminopyridines

图式11. 苯炔与2-酰胺基吡啶的去芳构化反应

Scheme 11. Dearomatization reaction of arynes and 2-amidylpyridines

图式12. HDDA苯炔与氮杂芳烃的去芳构化反应

Scheme 12. Dearomatization reaction of HDDA arynes and azaarenes

图式13. 苯炔与N-对甲苯磺酰胺基吡啶盐的[3+2]环加成反应

Scheme 13. [3+2] cycloaddition reaction of arynes with N- tosylpyridinium amides

图式14. 苯炔与吡啶叶立德的[3+2]环加成反应

Scheme 14. [3+2] cycloaddition reaction of arynes with pyridine ylides

图式15. 苯炔与喹啉氮氧化物的[3+2]环加成反应

Scheme 15. [3+2] cycloaddition reaction of arynes with quinoline N-oxides

图式16. 苯炔与双烯体的[4+2]环加成反应

Scheme 16. [4+2] cycloaddition reaction of arynes and dienes

图式17. 苯并噁二硅氧烷生成的苯炔与呋喃的[4+2]环加成反应

Scheme 17. [4+2] cycloaddition reactions of furans with arynes generated from benzooxadisiloles

图式18. 苯并噁二硅氧烷生成的苯炔与不同双烯体的[4+2]环加成反应

Scheme 18. [4+2] cycloaddition reaction of dienes with arynes generated from benzooxadisiloles

图式19. 不同苯炔前体与(异苯并)呋喃的[4+2]环加成反应

Scheme 19. [4+2] cycloaddition reaction of various aryne precursors with (isobenzo)furans

图式20. 苯炔与呋喃的分子内[4+2]环加成去芳构化反应

Scheme 20. Intramolecular [4+2] cycloaddition dearomatization reaction of arynes with furan

图式21. 苯炔与1,3-二苯乙炔基异苯并呋喃的[4+2]环加成反应

Scheme 21. [4+2] cycloaddition reaction of arynes with 1,3-bis(phenylethynyl)isobenzofuran

图式22. 苯炔与酚盐的分子内[4+2]环加成去芳构化反应

Scheme 22. Intramolecular [4+2] cycloaddition dearomatization reaction of arynes with Phenolates

图式23. 苯炔与氮甲基吡咯的[4+2]环加成串联反应

Scheme 23. Tandem [4+2] cycloaddition reaction of arynes with N-methylpyrrole

图式24. 苯炔与苯并呋喃的[4+2]/[2+2]环加成串联反应

Scheme 24. Tandem [4+2]/[2+2] cycloaddition reaction of arynes with benzofuran

图式25. 苯炔引发的[4+2]环加成反应合成isokidamycin

Scheme 25. Aryne induced [4+2] cycloaddition reaction in the synthesis of isokidamycin

图式26. 苯炔[4+2]环加成反应合成defucogilvocarcin M

Scheme 26. Aryne [4+2] cycloaddition reaction in the synthesis of defucogilvocarcin M

图式27. 苯炔引发的[4+2]环加成反应合成arnottins I和II

Scheme 27. Aryne induced [4+2] cycloaddition reaction in the synthesis of arnottins I and II

图式28. 苯炔引发的[4+2]环加成反应合成rifsaliniketal

Scheme 28. Aryne induced [4+2] cycloaddition reaction in the synthesis of rifsaliniketal

图式29. 卡宾介导的苯炔去芳构化反应

Scheme 29. Carbene mediated aryne-based dearomatization reactions

图式30. 钯催化的苯炔插入去芳构化反应

Scheme 30. Palladium-catalyzed dearomative aryne insertion reactions

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