Literature DB >> 22612535

Palladium-catalyzed aerobic oxidative cyclization of N-aryl imines: indole synthesis from anilines and ketones.

Ye Wei1, Indubhusan Deb, Naohiko Yoshikai.   

Abstract

We report here an operationally simple, palladium-catalyzed cyclization reaction of N-aryl imines, affording indoles via the oxidative linkage of two C-H bonds under mild conditions using molecular oxygen as the sole oxidant. The process allows quick and atom-economical assembly of indole rings from inexpensive and readily available anilines and ketones and tolerates a broad range of functional groups.

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Year:  2012        PMID： 22612535     DOI： 10.1021/ja3030824

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  20 in total

1.  Catalytic Synthesis of Substituted Indoles and Quinolines from the Dehydrative C-H Coupling of Arylamines with 1,2- and 1,3-Diols.

Authors:  Hanbin Lee; Chae S Yi
Journal:  Organometallics       Date:  2016-05-27       Impact factor: 3.876

2.  Structure-Activity Study of Bioisosteric Trifluoromethyl and Pentafluorosulfanyl Indole Inhibitors of the AAA ATPase p97.

Authors:  Celeste Alverez; Michelle R Arkin; Stacie L Bulfer; Raffaele Colombo; Marina Kovaliov; Matthew G LaPorte; Chaemin Lim; Mary Liang; William J Moore; R Jeffrey Neitz; Yongzhao Yan; Zhizhou Yue; Donna M Huryn; Peter Wipf
Journal:  ACS Med Chem Lett       Date:  2015-10-23       Impact factor: 4.345

3.  Synthesis of indoles, indolines, and carbazoles via palladium-catalyzed C─H activation.

Authors:  Alexander J Rago; Guangbin Dong
Journal:  Green Synth Catal       Date:  2021-03-04

4.  Copper-Catalyzed Synthesis of N-Aryl and N-Sulfonyl Indoles from 2-Vinylanilines with O2 as Terminal Oxidant and TEMPO as Co-Catalyst.

Authors:  Timothy W Liwosz; Sherry R Chemler
Journal:  Synlett       Date:  2014       Impact factor: 2.454

5.  Pd-catalyzed Semmler-Wolff reactions for the conversion of substituted cyclohexenone oximes to primary anilines.

Authors:  Wan Pyo Hong; Andrei V Iosub; Shannon S Stahl
Journal:  J Am Chem Soc       Date:  2013-09-04       Impact factor: 15.419

6.  Microwave-assisted synthesis of 3-nitroindoles from N-aryl enamines via intramolecular arene-alkene coupling.

Authors:  Huy H Nguyen; Mark J Kurth
Journal:  Org Lett       Date:  2012-12-26       Impact factor: 6.005

7.  Aerobic dehydrogenation of cyclohexanone to phenol catalyzed by Pd(TFA)2/2-dimethylaminopyridine: evidence for the role of Pd nanoparticles.

Authors:  Doris Pun; Tianning Diao; Shannon S Stahl
Journal:  J Am Chem Soc       Date:  2013-05-24       Impact factor: 15.419

8.  Palladium(II)-Catalyzed Tandem Oxidative Acetoxylation/ortho C-H Activation/Carbocyclization of Arylallenes.

Authors:  Javier Mazuela; Debasis Banerjee; Jan-E Bäckvall
Journal:  J Am Chem Soc       Date:  2015-07-28       Impact factor: 15.419

9.  Palladium-catalyzed oxidative acyloxylation/carbocyclization of allenynes.

Authors:  Youqian Deng; Jan-E Bäckvall
Journal:  Angew Chem Int Ed Engl       Date:  2013-02-05       Impact factor: 15.336

10.  Regioselective Mercury(I)/Palladium(II)-Catalyzed Single-Step Approach for the Synthesis of Imines and 2-Substituted Indoles.

Authors:  Rsuini U Gutiérrez; Mayra Hernández-Montes; Aarón Mendieta-Moctezuma; Francisco Delgado; Joaquín Tamariz
Journal:  Molecules       Date:  2021-07-05       Impact factor: 4.411
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