Literature DB >> 30576149

Cu-Catalyzed Oxidation of C2 and C3 Alkyl-Substituted Indole via Acyl Nitroso Reagents.

Jun Zhang1, Saeedeh Torabi Kohlbouni1, Babak Borhan1.   

Abstract

The selective oxidation of C2-alkyl-substituted indoles to 3-oxindole and the selective C-H oxygenation or amination of C2,C3-dialkyl-substituted indoles at C2 are reported under mild conditions. The position of the alkyl substitution on the indole directs the reaction to different pathways under similar conditions.

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Year:  2018        PMID： 30576149      PMCID： PMC7774803          DOI： 10.1021/acs.orglett.8b03185

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


  20 in total

Review 1.  The nitroso ene reaction: a regioselective and stereoselective allylic nitrogen functionalization of mechanistic delight and synthetic potential.

Authors:  Waldemar Adam; Oliver Krebs
Journal:  Chem Rev       Date:  2003-10       Impact factor: 60.622

2.  Copper-catalyzed aerobic oxidation of hydroxamic acids leads to a mild and versatile acylnitroso ene reaction.

Authors:  Charles P Frazier; Jarred R Engelking; Javier Read de Alaniz
Journal:  J Am Chem Soc       Date:  2011-06-16       Impact factor: 15.419

3.  Catalytic Asymmetric Oxidative α-C-H N,O-Ketalization of Ketones by Chiral Primary Amine.

Authors:  Changming Xu; Long Zhang; Sanzhong Luo
Journal:  Org Lett       Date:  2015-08-21       Impact factor: 6.005

4.  Indole Synthesis via Cyclative Formation of 2,3-Dizincioindoles and Regioselective Electrophilic Trapping.

Authors:  Laurean Ilies; Mayuko Isomura; Shin-Ichi Yamauchi; Tomoya Nakamura; Eiichi Nakamura
Journal:  J Am Chem Soc       Date:  2016-12-28       Impact factor: 15.419

5.  Copper(II)-catalyzed room temperature aerobic oxidation of hydroxamic acids and hydrazides to acyl-nitroso and azo intermediates, and their Diels-Alder trapping.

Authors:  Duangduan Chaiyaveij; Leah Cleary; Andrei S Batsanov; Todd B Marder; Kenneth J Shea; Andrew Whiting
Journal:  Org Lett       Date:  2011-06-06       Impact factor: 6.005

6.  Oxidative Dearomatization of Indoles via Pd-Catalyzed C-H Oxygenation: An Entry to C2-Quaternary Indolin-3-ones.

Authors:  Sankar K Guchhait; Vikas Chaudhary; Vijay A Rana; Garima Priyadarshani; Somnath Kandekar; Maneesh Kashyap
Journal:  Org Lett       Date:  2016-03-17       Impact factor: 6.005

7.  Base-Mediated Fragmentation of Bicyclic Dihydro-3,6-oxazines: Transformation of Nitroso Diels-Alder Cycloadducts.

Authors:  Rémy Campagne; Friederike Schäkel; Régis Guillot; Valérie Alezra; Cyrille Kouklovsky
Journal:  Org Lett       Date:  2018-03-09       Impact factor: 6.005

8.  Creation of molecular complexities via a new Cu-catalyzed cascade reaction: a direct access to novel 2,2'-spirobiindole derivatives.

Authors:  Bagineni Prasad; Raju Adepu; Atul Kumar Sharma; Manojit Pal
Journal:  Chem Commun (Camb)       Date:  2015-01-25       Impact factor: 6.222

9.  Highly Functionalized Tricyclic Oxazinanones via Pairwise Oxidative Dearomatization and N-Hydroxycarbamate Dehydrogenation: Molecular Diversity Inspired by Tetrodotoxin.

Authors:  Steffen N Good; Robert J Sharpe; Jeffrey S Johnson
Journal:  J Am Chem Soc       Date:  2017-08-30       Impact factor: 15.419

Review 10.  Biomedical importance of indoles.

Authors:  Nagendra Kumar Kaushik; Neha Kaushik; Pankaj Attri; Naresh Kumar; Chung Hyeok Kim; Akhilesh Kumar Verma; Eun Ha Choi
Journal:  Molecules       Date:  2013-06-06       Impact factor: 4.411
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