Literature DB >> 16928082

Solventless clay-promoted Friedel-Crafts reaction of indoles with alpha-amido sulfones: unexpected synthesis of 3-(1-arylsulfonylalkyl) indoles.

Roberto Ballini1, Alessandro Palmieri, Marino Petrini, Elisabetta Torregiani.   

Abstract

Friedel-Crafts reaction of indoles with alpha-amido sulfones in the presence of montmorillonite K-10 leads unexpectedly to 3-(1-arylsulfonylalkyl) indoles in good yield. The obtained products can be further desulfonylated under reductive or alkylative conditions giving linear and branched 3-substituted indoles.

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Year:  2006        PMID： 16928082     DOI： 10.1021/ol061604w

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


  6 in total

1.  Chiral Brønsted base-promoted nitroalkane alkylation: enantioselective synthesis of sec-alkyl-3-substituted indoles.

Authors:  Mark C Dobish; Jeffrey N Johnston
Journal:  Org Lett       Date:  2010-11-19       Impact factor: 6.005

2.  Direct organocatalytic coupling of carboxylated piperazine-2,5-diones with indoles through conjugate addition of carbon nucleophiles to indolenine intermediates.

Authors:  Ramin Dubey; Bogdan Olenyuk
Journal:  Tetrahedron Lett       Date:  2010-01-27       Impact factor: 2.415

Review 3.  Arenesulfonyl indole: new precursor for diversification of C-3 functionalized indoles.

Authors:  Banni Preet Kaur; Jasneet Kaur; Swapandeep Singh Chimni
Journal:  RSC Adv       Date:  2021-01-08       Impact factor: 3.361

Review 4.  1-Aminoalkylphosphonium Derivatives: Smart Synthetic Equivalents of N-Acyliminium-Type Cations, and Maybe Something More: A Review.

Authors:  Jakub Adamek; Mirosława Grymel; Anna Kuźnik; Agnieszka Październiok-Holewa
Journal:  Molecules       Date:  2022-02-26       Impact factor: 4.411

5.  Generation and Reactivity of 1-Imidocarbenium Cations in the Friedel-Crafts-type Reaction.

Authors:  Jakub Adamek; Roman Mazurkiewicz; Anna Węgrzyk-Schlieter
Journal:  ACS Omega       Date:  2022-08-15

6.  1-(N-Acylamino)alkyltriarylphosphonium Salts with Weakened Cα-P⁺ Bond Strength-Synthetic Applications.

Authors:  Jakub Adamek; Anna Węgrzyk; Justyna Kończewicz; Krzysztof Walczak; Karol Erfurt
Journal:  Molecules       Date:  2018-09-25       Impact factor: 4.411
  6 in total

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