Literature DB >> 17595097

Palladium-catalyzed C-H activation/intramolecular amination reaction: a new route to 3-aryl/alkylindazoles.

Kiyofumi Inamoto1, Tadataka Saito, Mika Katsuno, Takao Sakamoto, Kou Hiroya.   

Abstract

A method for the catalytic C-H activation of hydrazone compounds followed by intramolecular amination is described. It requires the use of a catalytic amount of Pd(OAc)2 in the presence of Cu(OAc)2 and AgOCOCF3, which efficiently effects the cyclization to afford variously substituted indazoles. The reactions proceed under relatively mild conditions and thus tolerate a variety of functional groups, including alkoxycarbonyl and cyano groups and halogen atoms.

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Year:  2007        PMID: 17595097     DOI: 10.1021/ol0711117

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  22 in total

1.  Heterocycle Formation via Palladium-Catalyzed C-H Functionalization.

Authors:  Tian-Sheng Mei; Lei Kou; Sandy Ma; Keary M Engle; Jin-Quan Yu
Journal:  Synthesis (Stuttg)       Date:  2012-05-25       Impact factor: 3.157

2.  Twofold C-H functionalization: palladium-catalyzed ortho arylation of anilides.

Authors:  Gordon Brasche; Jorge García-Fortanet; Stephen L Buchwald
Journal:  Org Lett       Date:  2008-05-09       Impact factor: 6.005

3.  Synthesis of Indole-2-carboxylate Derivatives via Palladium-Catalyzed Aerobic Amination of Aryl C-H Bonds.

Authors:  Kyle Clagg; Haiyun Hou; Adam B Weinstein; David Russell; Shannon S Stahl; Stefan G Koenig
Journal:  Org Lett       Date:  2016-07-12       Impact factor: 6.005

4.  Dirhodium-catalyzed C-H arene amination using hydroxylamines.

Authors:  Mahesh P Paudyal; Adeniyi Michael Adebesin; Scott R Burt; Daniel H Ess; Zhiwei Ma; László Kürti; John R Falck
Journal:  Science       Date:  2016-09-09       Impact factor: 47.728

5.  Heterocycle synthesis via direct C-H/N-H coupling.

Authors:  Enrico T Nadres; Olafs Daugulis
Journal:  J Am Chem Soc       Date:  2011-12-29       Impact factor: 15.419

Review 6.  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

7.  Palladium Catalyzed Aryl C-H Amination with O2 via In Situ Formation of Peroxide-Based Oxidant(s) from Dioxane.

Authors:  Adam B Weinstein; Shannon S Stahl
Journal:  Catal Sci Technol       Date:  2014-12-01       Impact factor: 6.119

8.  Directed amination of non-acidic arene C-H bonds by a copper-silver catalytic system.

Authors:  Ly Dieu Tran; James Roane; Olafs Daugulis
Journal:  Angew Chem Int Ed Engl       Date:  2013-04-24       Impact factor: 15.336

9.  Insights into directing group ability in palladium-catalyzed C-H bond functionalization.

Authors:  Lopa V Desai; Kara J Stowers; Melanie S Sanford
Journal:  J Am Chem Soc       Date:  2008-09-10       Impact factor: 15.419

10.  Palladium-catalyzed method for the synthesis of carbazoles via tandem C-H functionalization and C-N bond formation.

Authors:  W C Peter Tsang; Rachel H Munday; Gordon Brasche; Nan Zheng; Stephen L Buchwald
Journal:  J Org Chem       Date:  2008-08-29       Impact factor: 4.354

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