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Literature DB >> 17346056

Remarkably mild and efficient intramolecular Friedel-Crafts cyclization catalyzed by In(III).

Abstract

[structure: see text]. Indium(III) salts were found to be highly effective catalysts for the intramolecular Friedel-Crafts reaction of simple allylic bromides and arenes. In(III) salts appear to be the most general and possess unique halophilic properties as a Lewis acid for this reaction among the catalysts evaluated to date. Deactivated arenes possessing chloride, bromide, and fluoride underwent smooth reaction when activated by InCl3.

Entities: Chemical

Mesh：

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Year: 2007 PMID： 17346056 PMCID： PMC2553353 DOI： 10.1021/ol070235g

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

4 in total

1. New catalytic approaches in the stereoselective Friedel-Crafts alkylation reaction.

Authors: Marco Bandini; Alfonso Melloni; Achille Umani-Ronchi
Journal: Angew Chem Int Ed Engl Date: 2004-02-01 Impact factor: 15.336

2. Synthesis of azapolycyclic systems via the intramolecular [4 + 2] cycloaddition chemistry of 2-(alkylthio)-5-amidofurans.

Authors: Albert Padwa; John D Ginn; Scott K Bur; Cheryl K Eidell; Stephen M Lynch
Journal: J Org Chem Date: 2002-05-17 Impact factor: 4.354

3. InBr3-catalyzed Friedel-Crafts addition of indoles to chiral aromatic epoxides: a facile route to enantiopure indolyl derivatives.

Authors: Marco Bandini; Pier Giorgio Cozzi; Paolo Melchiorre; Achille Umani-Ronchi
Journal: J Org Chem Date: 2002-07-26 Impact factor: 4.354

4. Atom transfer cyclization catalyzed by InCl3 via halogen activation.

Authors: Gregory R Cook; Ryuji Hayashi
Journal: Org Lett Date: 2006-03-16 Impact factor: 6.005

4 in total

6 in total

Remarkably mild and efficient intramolecular Friedel-Crafts cyclization catalyzed by In(III).

1. New catalytic approaches in the stereoselective Friedel-Crafts alkylation reaction.

2. Synthesis of azapolycyclic systems via the intramolecular [4 + 2] cycloaddition chemistry of 2-(alkylthio)-5-amidofurans.

3. InBr3-catalyzed Friedel-Crafts addition of indoles to chiral aromatic epoxides: a facile route to enantiopure indolyl derivatives.

4. Atom transfer cyclization catalyzed by InCl3 via halogen activation.

1. Stereoselective 6π-electron electrocyclic ring closures of 2-halo-amidotrienes via a remote 1,6-asymmetric induction.

2. Concise total syntheses of aspalathin and nothofagin.

3. Enantioselective and regioselective indium(III)-catalyzed addition of pyrroles to isatins.

4. Gold(I)-catalyzed intramolecular hydroarylation of allenes.

5. Bi(OTf)(3)-Catalyzed 5-Exo-Trig Cyclization via Halide Activation.

Review 6. InCl₃: A Versatile Catalyst for Synthesizing a Broad Spectrum of Heterocycles.

Review 6. InCl3: A Versatile Catalyst for Synthesizing a Broad Spectrum of Heterocycles.

Review 6. InCl₃: A Versatile Catalyst for Synthesizing a Broad Spectrum of Heterocycles.