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Literature DB >> 23589402

Rhodium(III)-catalyzed synthesis of cinnolinium salts from azobenzenes and alkynes: application to the synthesis of indoles and cinnolines.

Krishnamoorthy Muralirajan¹, Chien-Hong Cheng.

Abstract

Versatile salts: A new rhodium-catalyzed synthesis of cinnolinium salts from various azobenzenes and alkynes under air is described. These salts readily transform into three important classes of products, including indoles, indoloindoles, and cinnolines (see scheme).

Entities: Chemical

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Year: 2013 PMID： 23589402 DOI： 10.1002/chem.201300922

Source DB: PubMed Journal: Chemistry ISSN： 0947-6539 Impact factor: 5.236

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Cited

6 in total

1. Facile synthesis of unsymmetrical acridines and phenazines by a Rh(III)-catalyzed amination/cyclization/aromatization cascade.

Authors: Yajing Lian; Joshua R Hummel; Robert G Bergman; Jonathan A Ellman
Journal: J Am Chem Soc Date: 2013-08-19 Impact factor: 15.419

2. Catalytic 1,4-rhodium(III) migration enables 1,3-enynes to function as one-carbon oxidative annulation partners in C-H functionalizations.

Authors: David J Burns; Hon Wai Lam
Journal: Angew Chem Int Ed Engl Date: 2014-07-22 Impact factor: 15.336

Rhodium(III)-catalyzed synthesis of cinnolinium salts from azobenzenes and alkynes: application to the synthesis of indoles and cinnolines.

1. Facile synthesis of unsymmetrical acridines and phenazines by a Rh(III)-catalyzed amination/cyclization/aromatization cascade.

2. Catalytic 1,4-rhodium(III) migration enables 1,3-enynes to function as one-carbon oxidative annulation partners in C-H functionalizations.

3. Asymmetric synthesis of α-branched amines via Rh(III)-catalyzed C-H bond functionalization.

4. Rhodium-catalyzed C-H functionalization-based approach to eight-membered lactams.

5. Cobalt(III)-catalyzed synthesis of indazoles and furans by C-H bond functionalization/addition/cyclization cascades.

6. Tuneable access to indole, indolone, and cinnoline derivatives from a common 1,4-diketone Michael acceptor.