Recent Progress in Aryne Participated Dearomatization Reactions

doi:10.6023/cjoc202009009

Abstract

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

Cite this article

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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Fig. & Tab. 30

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

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

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

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

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

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

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

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

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

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

Scheme 11. Dearomatization reaction of arynes and 2-amidylpyridines

Scheme 12. Dearomatization reaction of HDDA arynes and azaarenes

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Scheme 29. Carbene mediated aryne-based dearomatization reactions

Scheme 30. Palladium-catalyzed dearomative aryne insertion reactions

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