Lewis Acid-Catalyzed Selective [2 + 2]-Cycloaddition and Dearomatizing Cascade Reaction of Aryl Alkynes with Acrylates

Research output: Journal Publications and Reviews (RGC: 21, 22, 62)21_Publication in refereed journalNot applicablepeer-review

20 Scopus Citations
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Author(s)

  • Liang Shen
  • Kai Zhao
  • Kazuki Doitomi
  • Rakesh Ganguly
  • Yong-Xin Li
  • Zhi-Liang Shen
  • Teck-Peng Loh

Related Research Unit(s)

Detail(s)

Original languageEnglish
Pages (from-to)13570-13578
Journal / PublicationJournal of the American Chemical Society
Volume139
Issue number38
Early online date7 Sep 2017
Publication statusPublished - 27 Sep 2017

Abstract

Combined Lewis acid, consisting of two or more Lewis acids, sometimes shows unique catalytic ability, and it may promote reactions which could not be catalyzed by any of the Lewis acids solely. On the other hand, the development of efficient methods for the facile synthesis of cyclobutenes and densely functionalized decalins is an attractive target for synthetic chemists due to their versatile synthetic utilities and widespread occurrence in natural products. Herein, we wish to report an efficient method for the assembly of cyclobutenes and densely functionalized decalin skeletons through In(tfacac)3- TMSBr catalyzed selective [2 + 2]-cycloaddition and dearomatizing cascade reaction of aryl alkynes with acrylates with high chemo- and stereoselectivity. The obtained cyclobutene could be easily converted into cyclobutane as well as synthetically useful 1,4- and 1,5-diketones with high chemo- and stereoselectivity. On the basis of mechanistic studies, plausible reaction mechanisms were proposed for both the [2 + 2]-cycloaddition and the dearomatizing cascade reaction. Finally, the computational studies of reaction mechanisms were conducted, and the results suggest that the combined Lewis acid could efficiently promote both reactions.

Citation Format(s)

Lewis Acid-Catalyzed Selective [2 + 2]-Cycloaddition and Dearomatizing Cascade Reaction of Aryl Alkynes with Acrylates. / Shen, Liang; Zhao, Kai; Doitomi, Kazuki; Ganguly, Rakesh; Li, Yong-Xin; Shen, Zhi-Liang; Hirao, Hajime; Loh, Teck-Peng.

In: Journal of the American Chemical Society, Vol. 139, No. 38, 27.09.2017, p. 13570-13578.

Research output: Journal Publications and Reviews (RGC: 21, 22, 62)21_Publication in refereed journalNot applicablepeer-review