Harnessing the Polarizability of Conjugated Alkynes toward [2 + 2] Cycloaddition, Alkenylation, and Ring Expansion of Indoles

Organic Letters
Tapas R PradhanJin Kyoon Park

Abstract

Reported is the utilization of electronically biased conjugated alkynes in the development of highly diastereo- and regioselective dearomative [2 + 2] cycloadditions, alkenylations, and ring expansions of electron-rich indoles. Regioselective protonations of cross- and linear-conjugated alkynes were found to be crucial for accessing various cyclobutene-fused indoline and alkenylated indole derivatives. Furthermore, the facile ring expansion of [2 + 2] keto adducts, which were successfully synthesized from ynones, provided 1 H-benzo[ b]azepine scaffolds.

References

Dec 1, 1993·Proceedings of the National Academy of Sciences of the United States of America·C B Gorman, S R Marder
Apr 9, 2004·Journal of the American Chemical Society·Hisanaka ItoKazuo Iguchi
Jun 17, 2004·Journal of the American Chemical Society·Randy F SweisSergey A Kozmin
Sep 10, 2004·Journal of the American Chemical Society·Tuanli YaoRichard C Larock
Sep 16, 2004·Chemical Communications : Chem Comm·J S YadavB Jagadeesh
Mar 18, 2005·Journal of the American Chemical Society·Kazato InanagaMasataka Ihara
Jun 9, 2005·Journal of the American Chemical Society·Alois FürstnerTobias Gress
May 16, 2008·Chemical Reviews·Pablo Wessig, Gunnar Müller
May 23, 2008·Journal of the American Chemical Society·Kazuaki Ishihara, Makoto Fushimi
Mar 3, 2010·Journal of the American Chemical Society·Wei ZhangWeiping Tang
May 6, 2010·Journal of the American Chemical Society·Derek J SchipperKeith Fagnou
Jun 24, 2010·Journal of the American Chemical Society·Verónica López-Carrillo, Antonio M Echavarren
Jul 16, 2010·Angewandte Chemie·Frédéric FrébaultNuno Maulide
Aug 10, 2010·Organic Letters·Hongyan LiYonggang Wei
Oct 15, 2010·Journal of the American Chemical Society·Annie Butler RicksMichael R Wasielewski
Apr 5, 2012·Angewandte Chemie·Zhenhua Ding, Naohiko Yoshikai
Sep 13, 2012·Journal of the American Chemical Society·Akira NishimuraSensuke Ogoshi
Jan 13, 2015·Chemical Communications : Chem Comm·Renxiao LiangShifa Zhu
Jul 12, 2017·Angewandte Chemie·David KosslerNicolai Cramer
Sep 20, 2017·Journal of the American Chemical Society·Cristina García-MoralesAntonio M Echavarren
Jul 1, 2015·Chemical Science·Charlie Verrier, Paolo Melchiorre
Apr 6, 2018·Journal of the American Chemical Society·Yu-Bin BaiLiming Zhang

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Citations

Nov 20, 2019·Chemical Communications : Chem Comm·Kunhua XuXu Tian
May 20, 2020·Nature Communications·Sujin HaCheol-Min Park

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