Literature DB >> 19415704

Stereoselective palladium-catalyzed carboaminoxylations of indoles with arylboronic acids and TEMPO.

Sylvia Kirchberg1, Roland Fröhlich, Armido Studer.   

Abstract

Indoles are not indolent: Various indoles react with arylboronic acids chemodivergently. C-H arylation of free indole and N-methylindole gives the corresponding C(2)-arylated indoles A whereas N-acylated, N-benzoylated, and N-Boc-protected indoles provide the corresponding arylcarboaminoxylated products B with excellent diastereoselectivity in good to excellent yields.

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Year:  2009        PMID： 19415704     DOI： 10.1002/anie.200901072

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  9 in total

1.  Palladium-Catalyzed C-H Arylation Using Aryltrifluoroborates in Conjunction with a MnIII Oxidant under Mild Conditions.

Authors:  Cydney K Seigerman; Tiffiny M Micyus; Sharon R Neufeldt; Melanie S Sanford
Journal:  Tetrahedron       Date:  2013-07-08       Impact factor: 2.457

2.  Ligand-accelerated cross-coupling of C(sp2)-H bonds with arylboron reagents.

Authors:  Keary M Engle; Peter S Thuy-Boun; Michael Dang; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2011-10-21       Impact factor: 15.419

3.  Ru-catalysed C-H arylation of indoles and pyrroles with boronic acids: scope and mechanistic studies.

Authors:  Carina Sollert; Karthik Devaraj; Andreas Orthaber; Paul J Gates; Lukasz T Pilarski
Journal:  Chemistry       Date:  2015-02-17       Impact factor: 5.236

4.  Stoichiometric to catalytic reactivity of the aryl cycloaurated species with arylboronic acids: insight into the mechanism of gold-catalyzed oxidative C(sp2)-H arylation.

Authors:  Qian Wu; Chenglong Du; Yumin Huang; Xingyan Liu; Zhen Long; Feijie Song; Jingsong You
Journal:  Chem Sci       Date:  2014-10-09       Impact factor: 9.825

5.  Catalyst-Controlled Regioselectivity in Pd-Catalyzed Aerobic Oxidative Arylation of Indoles.

Authors:  Dian Wang; Chase A Salazar; Shannon S Stahl
Journal:  Organometallics       Date:  2021-04-08       Impact factor: 3.837

6.  Development of Stereocontrolled Palladium(II)-Catalyzed Domino Heck/Suzuki β,α-Diarylation Reactions with Chelating Vinyl Ethers and Arylboronic Acids.

Authors:  Alejandro Trejos; Luke R Odell; Mats Larhed
Journal:  ChemistryOpen       Date:  2012-02       Impact factor: 2.911

7.  Metal-free borylative dearomatization of indoles: exploring the divergent reactivity of aminoborane C-H borylation catalysts.

Authors:  Arumugam Jayaraman; Luis C Misal Castro; Vincent Desrosiers; Frédéric-Georges Fontaine
Journal:  Chem Sci       Date:  2018-05-07       Impact factor: 9.825

8.  Rhodium catalyzed diastereoselective synthesis of 2,2,3,3-tetrasubstituted indolines from N-sulfonyl-1,2,3-triazoles and ortho-vinylanilines.

Authors:  Dongari Yadagiri; Angula Chandra Shekar Reddy; Pazhamalai Anbarasan
Journal:  Chem Sci       Date:  2016-05-24       Impact factor: 9.825

9.  Simplification of Natural β-Carboline Alkaloids to Obtain Indole Derivatives as Potent Fungicides against Rice Sheath Blight.

Authors:  Jie Zeng; Zhijun Zhang; Qi Zhu; Zhiyan Jiang; Guohua Zhong
Journal:  Molecules       Date:  2020-03-06       Impact factor: 4.411
  9 in total

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