Metal-free synthesis of indole via NIS-mediated cascade C-N bond formation/aromatization

The Journal of Organic Chemistry
Yin-Long LiJun Deng

Abstract

A novel rapid synthesis of indoles from N-Ts-2-alkenylanilines has been described; the reaction involves a NIS-mediated cascade C-N bond formation/aromatization, and a series of indoles with various functional groups have been synthesized in good to excellent yields under mild conditions without any other additives or catalysts.

References

May 31, 1996·The Journal of Organic Chemistry·Richard C. LarockKarl P. Peterson
Mar 26, 2004·Natural Product Reports·Masanori Somei, Fumio Yamada
May 13, 2004·Chemical Reviews·Itaru Nakamura, Yoshinori Yamamoto
Jul 14, 2005·Chemical Reviews·Sandro Cacchi, Giancarlo Fabrizi
Jul 14, 2006·Chemical Reviews·Guy R Humphrey, Jeffrey T Kuethe
Nov 1, 2006·Angewandte Chemie·K C NicolaouPaul G Bulger
May 26, 2007·Journal of the American Chemical Society·Benjamin J StokesTom G Driver
Jun 9, 2007·The Journal of Organic Chemistry·Benedikt Crone, Stefan F Kirsch
Apr 30, 2008·Angewandte Chemie·Tao PeiIan W Davies
May 31, 2008·Angewandte Chemie·Meihua ShenTom G Driver
Sep 19, 2008·Journal of the American Chemical Society·Sun-Liang CuiYan-Guang Wang
Apr 11, 2009·Chemistry, an Asian Journal·José BarluengaFrancisco J Fañanás
Oct 23, 2009·Chemical Society Reviews·K C Nicolaou, Jason S Chen
Dec 1, 2009·Angewandte Chemie·Marco Bandini, Astrid Eichholzer
Apr 13, 2010·Chemical Reviews·Anna J Kochanowska-Karamyan, Mark T Hamann
Jun 8, 2010·The Journal of Organic Chemistry·Zhiheng HeZhiping Li
Aug 31, 2010·Angewandte Chemie·Gemma E Veitch, Eric N Jacobsen
Dec 8, 2010·Journal of the American Chemical Society·David R StuartKeith Fagnou
May 12, 2011·Chemical Reviews·Sandro Cacchi, Giancarlo Fabrizi
Jun 16, 2011·Organic Letters·Donald McAuslandMichael F Greaney
Jan 31, 2012·The Journal of Organic Chemistry·Chandra Bhushan Tripathi, Santanu Mukherjee
Mar 7, 2012·Chemical Reviews·Morteza Shiri
Apr 3, 2012·Journal of the American Chemical Society·Mark C Dobish, Jeffrey N Johnston
May 15, 2012·Accounts of Chemical Research·Liang-Qiu LuWen-Jing Xiao
Aug 24, 2012·Journal of the American Chemical Society·Nicklas SelanderValery V Fokin
Nov 15, 2012·Organic Letters·Jørn E TungenTrond V Hansen
Dec 26, 2012·Journal of the American Chemical Society·Quyen NguyenTom G Driver
Feb 16, 2013·The Journal of Organic Chemistry·Florian Huber, Stefan F Kirsch

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Citations

May 11, 2016·The Journal of Organic Chemistry·Ya-Nan HuangJun Deng
Aug 18, 2016·The Journal of Organic Chemistry·Manikandan ThangarajAkkattu T Biju
May 24, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Ruizhi GuoXiaodan Zhao
Jul 7, 2017·The Journal of Organic Chemistry·Sindhura Badigenchala, Govindasamy Sekar
Mar 17, 2018·Organic & Biomolecular Chemistry·Nuannuan MaChangwen Hu
Apr 11, 2020·Organic Letters·Amol Milind GarkhedkarJeh-Jeng Wang

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