+ Site Statistics
+ Search Articles
+ PDF Full Text Service
How our service works
Request PDF Full Text
+ Follow Us
Follow on Facebook
Follow on Twitter
Follow on LinkedIn
+ Subscribe to Site Feeds
Most Shared
PDF Full Text
+ Translate
+ Recently Requested

A sequential metal-catalyzed C-N bond formation in the synthesis of 2-amido-indoles

A sequential metal-catalyzed C-N bond formation in the synthesis of 2-amido-indoles

Organic Letters 10(19): 4275-4278

A sequential metal-catalyzed C-N bond formation employing ortho-haloaryl acetylenic bromides is described. The initial amidation is highly selective for C (sp)-N bond formation, leading to o-haloaryl-substituted ynamides that can be useful building blocks, while the overall sequence provides a facile construction of 2-amido-indoles.

Please choose payment method:

(PDF emailed within 0-6 h: $19.90)

Accession: 051249905

Download citation: RISBibTeXText

PMID: 18754591

DOI: 10.1021/ol801711p

Related references

Copper-Catalyzed Dehydrogenative C(sp 2 )-N Bond Formation via Direct Oxidative Activation of an Anilidic N-H Bond: Synthesis of Benzoimidazo[1,2-a]indoles. Journal of Organic Chemistry 82(19): 10158-10166, 2017

Synthesis of Indoles via Electron-Catalyzed Intramolecular C-N Bond Formation. Organic Letters 2018, 2018

Copper-catalyzed C-C bond formation through C-H functionalization: synthesis of multisubstituted indoles from N-aryl enaminones. Angewandte Chemie 48(43): 8078-8081, 2010

Rh/Cu-catalyzed multiple C-H, C-C, and C-N bond cleavage: facile synthesis of pyrido[2,1-a]indoles from 1-(pyridin-2-yl)-1H-indoles and γ-substituted propargyl alcohols. Chemical Communications 51(31): 6777-6780, 2015

Synthesis of Substituted Benzo[b]thiophenes via Sequential One-Pot, Copper-Catalyzed Intermolecular C-S Bond Formation and Palladium-Catalyzed Intramolecular Arene-Alkene Coupling of Bis(het)aryl/alkyl-1,3-monothiodiketones and o-Bromoiodoarenes. Organic Letters 19(7): 1512-1515, 2017

Rh-catalyzed oxidative C-C bond formation and C-N bond cleavage: direct access to C2-olefinated free (NH)-indoles and pyrroles. Organic and Biomolecular Chemistry 12(11): 1703-1706, 2014

An efficient route to synthesize isatins by metal-free, iodine-catalyzed sequential C(sp(3))-H oxidation and intramolecular C-N bond formation of 2'-aminoacetophenones. Organic and Biomolecular Chemistry 12(42): 8512-8518, 2015

Synthesis of 1-Azaanthraquinone: Sequential C-N Bond Formation/Lewis Acid Catalyzed Intramolecular Cyclization Strategy. Journal of Organic Chemistry 82(15): 8309-8316, 2017

Divalent metal ion catalyzed pyrophosphate bond formation in aqueous solution synthesis of nucleotides containing polyphosphate. Nucleosides & Nucleotides 11(2-4): 773-785, 1992

The Synthesis of 1-Hydroxy Phosphonates of High Enantiomeric Excess Using Sequential Asymmetric Reactions: Titanium Alkoxide Catalyzed P--C Bond Formation and Kinetic Resolution. Phosphorus Sulfur and Silicon and the Related Elements 177(8-9): 1955-1955, 2002

Early transition metal-catalyzed C-H alkylation: hydroaminoalkylation for C sp 3 -C sp 3 bond formation in the synthesis of selectively substituted amines. Chemical Communications 54(89): 12543-12560, 2018

I 2 -Catalyzed Oxidative N-S Bond Formation: Metal-Free Regiospecific Synthesis of N-Fused and 3,4-Disubstituted 5-Imino-1,2,4-thiadiazoles. Journal of Organic Chemistry 82(10): 5310-5316, 2017

Solventless clay-promoted Friedel-Crafts reaction of indoles with alpha-amido sulfones: unexpected synthesis of 3-(1-arylsulfonylalkyl) indoles. Organic Letters 8(18): 4093-4096, 2006

Atom economical synthesis of oxindoles by metal-catalyzed intramolecular CC bond formation under solvent-free and aerobic conditions. Green Chemistry 17(6): 3306-3309, 2015

Intramolecular oxidative C-N bond formation for the synthesis of carbazoles: comparison of reactivity between the copper-catalyzed and metal-free conditions. Journal of the American Chemical Society 133(15): 5996-6005, 2011