Literature DB >> 19652690

Oxidant-controlled regioselectivity in the oxidative arylation of N-acetylindoles.

Shathaverdhan Potavathri1, Ashley S Dumas, Timothy A Dwight, Gregory R Naumiec, Jeffrey M Hammann, Brenton Deboef.   

Abstract

N-Acetylindoles can be oxidatively coupled with arenes such as benzene or pentafluorobenzene in dioxane. The use of Cu(OAc)(2) as the stoichiometric oxidant produces selective arylation at the 3-position of indole while AgOAc produces selective arylation at indole's 2-position.

Entities:  

Year:  2008        PMID： 19652690      PMCID： PMC2597825          DOI： 10.1016/j.tetlet.2008.04.073

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  15 in total

1.  Palladium-catalyzed intermolecular alkenylation of indoles by solvent-controlled regioselective C-H functionalization.

Authors:  Neil P Grimster; Carolyn Gauntlett; Christopher R A Godfrey; Matthew J Gaunt
Journal:  Angew Chem Int Ed Engl       Date:  2005-05-13       Impact factor: 15.336

2.  Direct C-arylation of free (NH)-indoles and pyrroles catalyzed by Ar-Rh(III) complexes assembled in situ.

Authors:  Xiang Wang; Benjamin S Lane; Dalibor Sames
Journal:  J Am Chem Soc       Date:  2005-04-13       Impact factor: 15.419

3.  Catalytic and highly regioselective cross-coupling of aromatic C-H substrates.

Authors:  Kami L Hull; Melanie S Sanford
Journal:  J Am Chem Soc       Date:  2007-09-11       Impact factor: 15.419

4.  Palladium-catalyzed C-H homocoupling of bromothiophene derivatives and synthetic application to well-defined oligothiophenes.

Authors:  Masabumi Takahashi; Kentaro Masui; Hiroki Sekiguchi; Nobuhiko Kobayashi; Atsunori Mori; Masahiro Funahashi; Nobuyuki Tamaoki
Journal:  J Am Chem Soc       Date:  2006-08-23       Impact factor: 15.419

5.  Highly regioselective catalytic oxidative coupling reactions: synthetic and mechanistic investigations.

Authors:  Kami L Hull; Erica L Lanni; Melanie S Sanford
Journal:  J Am Chem Soc       Date:  2006-11-01       Impact factor: 15.419

6.  Elements of regiocontrol in palladium-catalyzed oxidative arene cross-coupling.

Authors:  David R Stuart; Elisia Villemure; Keith Fagnou
Journal:  J Am Chem Soc       Date:  2007-09-19       Impact factor: 15.419

7.  C-C bond formation via double C-H functionalization: aerobic oxidative coupling as a method for synthesizing heterocoupled biaryls.

Authors:  Timothy A Dwight; Nicholas R Rue; Dagmara Charyk; Ryan Josselyn; Brenton DeBoef
Journal:  Org Lett       Date:  2007-07-07       Impact factor: 6.005

8.  A general gold-catalyzed direct oxidative coupling of non-activated arenes.

Authors:  Anirban Kar; Naveenkumar Mangu; Hanns Martin Kaiser; Matthias Beller; Man Kin Tse
Journal:  Chem Commun (Camb)       Date:  2008-01-21       Impact factor: 6.222

9.  The catalytic cross-coupling of unactivated arenes.

Authors:  David R Stuart; Keith Fagnou
Journal:  Science       Date:  2007-05-25       Impact factor: 47.728

10.  Palladium-catalyzed arylation and heteroarylation of indolizines.

Authors:  Choul-Hong Park; Victoria Ryabova; Ilya V Seregin; Anna W Sromek; Vladimir Gevorgyan
Journal:  Org Lett       Date:  2004-04-01       Impact factor: 6.005
View more
  12 in total

1.  Regiocontrolled aerobic oxidative coupling of indoles and benzene using Pd catalysts with 4,5-diazafluorene ligands.

Authors:  Alison N Campbell; Eric B Meyer; Shannon S Stahl
Journal:  Chem Commun (Camb)       Date:  2011-08-22       Impact factor: 6.222

2.  Regioselective oxidative arylation of indoles bearing N-alkyl protecting groups: dual C-H functionalization via a concerted metalation-deprotonation mechanism.

Authors:  Shathaverdhan Potavathri; Kyle C Pereira; Serge I Gorelsky; Andrew Pike; Alexis P LeBris; Brenton DeBoef
Journal:  J Am Chem Soc       Date:  2010-10-20       Impact factor: 15.419

Review 3.  Bystanding F+ oxidants enable selective reductive elimination from high-valent metal centers in catalysis.

Authors:  Keary M Engle; Tian-Sheng Mei; Xisheng Wang; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2011-01-24       Impact factor: 15.336

4.  Controlling site selectivity in palladium-catalyzed C-H bond functionalization.

Authors:  Sharon R Neufeldt; Melanie S Sanford
Journal:  Acc Chem Res       Date:  2012-05-03       Impact factor: 22.384

5.  Palladium(III) in Synthesis and Catalysis.

Authors:  David C Powers; Tobias Ritter
Journal:  Top Organomet Chem       Date:  2011-01-01       Impact factor: 1.311

6.  Aerobic Oxidative Coupling of o-Xylene: Discovery of 2-Fluoropyridine as a Ligand to Support Selective Pd-Catalyzed C-H Functionalization.

Authors:  Yusuke Izawa; Shannon S Stahl
Journal:  Adv Synth Catal       Date:  2010-12-17       Impact factor: 5.837

7.  Insight into the palladium catalyzed oxidative arylation of benzofuran: Heteropoly acid oxidants evoke a Pd(II)/Pd(IV) mechanism.

Authors:  Kyle C Pereira; Ashley L Porter; Shathaverdhan Potavathri; Alec P Lebris; Brenton Deboef
Journal:  Tetrahedron       Date:  2013-06-01       Impact factor: 2.457

8.  Palladium-catalyzed dual C-H or N-H functionalization of unfunctionalized indole derivatives with alkenes and arenes.

Authors:  Gianluigi Broggini; Egle M Beccalli; Andrea Fasana; Silvia Gazzola
Journal:  Beilstein J Org Chem       Date:  2012-10-11       Impact factor: 2.883

9.  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

10.  Pd-catalyzed aerobic oxidative coupling of arenes: evidence for transmetalation between two Pd(II)-aryl intermediates.

Authors:  Dian Wang; Yusuke Izawa; Shannon S Stahl
Journal:  J Am Chem Soc       Date:  2014-06-30       Impact factor: 15.419
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.