Literature DB >> 21637891

Au-catalyzed synthesis of 2-alkylindoles from N-arylhydroxylamines and terminal alkynes.

Yanzhao Wang1, Longwu Ye, Liming Zhang.   

Abstract

The first gold-catalyzed addition of N-arylhydroxylamines to aliphatic terminal alkynes is developed to access O-alkenyl-N-arylhydroxylamines, which undergo facile in situ sequential 3,3-rearrangements and cyclodehydrations to afford 2-alkylindoles with regiospecificity and under exceptionally mild reaction conditions.

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Year:  2011        PMID： 21637891      PMCID： PMC3402563          DOI： 10.1039/c1cc12212f

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  15 in total

1.  Regiocontrol in an intramolecular Schmidt reaction: total synthesis of (+)-aspidospermidine.

Authors:  R Iyengar; K Schildknegt; J Aubé
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2.  Gold-catalyzed synthesis of 3-pyrrolidinones and nitrones from N-sulfonyl hydroxylamines via oxygen-transfer redox and 1,3-sulfonyl migration.

Authors:  Hyun-Suk Yeom; Eunsu So; Seunghoon Shin
Journal:  Chemistry       Date:  2011-01-05       Impact factor: 5.236

3.  Development of the [3 + 2] annulations of cyclohexenylsilanes and chlorosulfonyl isocyanate: application to the total synthesis of (+/-)-peduncularine.

Authors:  Claudia W Roberson; K A Woerpel
Journal:  J Am Chem Soc       Date:  2002-09-25       Impact factor: 15.419

4.  A two step route to indoles from haloarenes--a versatile variation on the Fischer indole synthesis.

Authors:  Martyn Inman; Christopher J Moody
Journal:  Chem Commun (Camb)       Date:  2010-11-22       Impact factor: 6.222

Review 5.  Practical methodologies for the synthesis of indoles.

Authors:  Guy R Humphrey; Jeffrey T Kuethe
Journal:  Chem Rev       Date:  2006-07       Impact factor: 60.622

6.  Total Synthesis of (+/-)-Deethylibophyllidine: Studies of a Fischer Indolization Route and a Successful Approach via a Pummerer Rearrangement/Thionium Ion-Mediated Indole Cyclization.

Authors:  Josep Bonjoch; Juanlo Catena; Nativitat Valls
Journal:  J Org Chem       Date:  1996-10-04       Impact factor: 4.354

7.  Gold-catalyzed organic reactions.

Authors:  A Stephen K Hashmi
Journal:  Chem Rev       Date:  2007-06-20       Impact factor: 60.622

8.  Total synthesis of (+)-haplophytine.

Authors:  Hirofumi Ueda; Hitoshi Satoh; Koji Matsumoto; Kenji Sugimoto; Tohru Fukuyama; Hidetoshi Tokuyama
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

9.  Heterocycles from gold catalysis.

Authors:  Matthias Rudolph; A Stephen K Hashmi
Journal:  Chem Commun (Camb)       Date:  2011-03-31       Impact factor: 6.222

10.  Carbocyclisation of alkynes with external nucleophiles catalysed by gold, platinum and other electrophilic metals.

Authors:  Shariar Md Abu Sohel; Rai-Shung Liu
Journal:  Chem Soc Rev       Date:  2009-04-29       Impact factor: 54.564
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  6 in total

1.  Rapid access to chroman-3-ones through gold-catalyzed oxidation of propargyl aryl ethers.

Authors:  Yanzhao Wang; Kegong Ji; Sylvester Lan; Liming Zhang
Journal:  Angew Chem Int Ed Engl       Date:  2012-01-13       Impact factor: 15.336

2.  One-pot synthesis of fused pyrroles through a key gold-catalysis-triggered cascade.

Authors:  Zhitong Zheng; Huangfei Tu; Liming Zhang
Journal:  Chemistry       Date:  2014-01-30       Impact factor: 5.236

3.  Combining Zn Ion Catalysis with Homogeneous Gold Catalysis: An Efficient Annulation Approach to N-Protected Indoles.

Authors:  Yanzhao Wang; Lianzhu Liu; Liming Zhang
Journal:  Chem Sci       Date:  2013-02-01       Impact factor: 9.825

Review 4.  Homogeneous Gold-Catalyzed Oxidation Reactions.

Authors:  Zhitong Zheng; Xu Ma; Xinpeng Cheng; Ke Zhao; Kaylaa Gutman; Tianyou Li; Liming Zhang
Journal:  Chem Rev       Date:  2021-02-16       Impact factor: 72.087

5.  Synthesis of Functionalized Indoles via Palladium-Catalyzed Cyclization of N-(2-allylphenyl) Benzamide: A Method for Synthesis of Indomethacin Precursor.

Authors:  Zhe Chang; Tong Ma; Yu Zhang; Zheng Dong; Heng Zhao; Depeng Zhao
Journal:  Molecules       Date:  2020-03-09       Impact factor: 4.411

6.  Acyl Migration versus Epoxidation in Gold Catalysis: Facile, Switchable, and Atom-Economic Synthesis of Acylindoles and Quinoline Derivatives.

Authors:  Xianhai Tian; Lina Song; Kaveh Farshadfar; Matthias Rudolph; Frank Rominger; Thomas Oeser; Alireza Ariafard; A Stephen K Hashmi
Journal:  Angew Chem Int Ed Engl       Date:  2019-11-26       Impact factor: 15.336
  6 in total

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