Literature DB >> 12889885

Bartoli indole synthesis on solid supports.

Kerstin Knepper1, Stefan Bräse.   

Abstract

[reaction: see text] Bartoli indole synthesis has been performed for the first time on solid supports. Starting from Merrifield resin, immobilization of five nitro benzoic acids was performed. Addition of four different alkenyl Grignard reagents and basic cleavage leads to substituted methyl indole carboxylates in excellent purities. Features of this reaction are the stability of halide groups, ester moieties, and tolerance of o,o'-unsubstituted nitro resins. Heck and Sonogashira reactions are also possible with immobilized indoles.

Entities:  

Year:  2003        PMID: 12889885     DOI: 10.1021/ol034851y

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


  2 in total

1.  Highly substituted indole library synthesis by palladium-catalyzed coupling reactions in solution and on a solid support.

Authors:  Shilpa A Worlikar; Benjamin Neuenswander; Gerald H Lushington; Richard C Larock
Journal:  J Comb Chem       Date:  2009 Sep-Oct

2.  Synthesis of diverse indole libraries on polystyrene resin - Scope and limitations of an organometallic reaction on solid supports.

Authors:  Kerstin Knepper; Sylvia Vanderheiden; Stefan Bräse
Journal:  Beilstein J Org Chem       Date:  2012-07-26       Impact factor: 2.883

  2 in total

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