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Knepper K, Vanderheiden S, Bräse S. Synthesis of diverse indole libraries on polystyrene resin - Scope and limitations of an organometallic reaction on solid supports. Beilstein J Org Chem. 2012;8:1191-9doi: 10.3762/bjoc.8.132.
Knepper, K., Vanderheiden, S., & Bräse, S. (2012). Synthesis of diverse indole libraries on polystyrene resin - Scope and limitations of an organometallic reaction on solid supports. Beilstein journal of organic chemistry, 81191-9. https://doi.org/10.3762/bjoc.8.132
Knepper, Kerstin, et al. "Synthesis of diverse indole libraries on polystyrene resin - Scope and limitations of an organometallic reaction on solid supports." Beilstein journal of organic chemistry vol. 8 (2012): 1191-9. doi: https://doi.org/10.3762/bjoc.8.132
Knepper K, Vanderheiden S, Bräse S. Synthesis of diverse indole libraries on polystyrene resin - Scope and limitations of an organometallic reaction on solid supports. Beilstein J Org Chem. 2012;8:1191-9. doi: 10.3762/bjoc.8.132. Epub 2012 Jul 26. PMID: 23019447; PMCID: PMC3458737.
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Beilstein J Org Chem. 2012;8:1191-9. doi: 10.3762/bjoc.8.132. Epub 2012 Jul 26.

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

Beilstein journal of organic chemistry

Kerstin Knepper, Sylvia Vanderheiden, Stefan Bräse

Affiliations

  1. Institute of Organic Chemistry, Karlsruhe Institute of Technology (KIT), Fritz-Haber-Weg 6, D-76131 Karlsruhe, Germany.

PMID: 23019447 PMCID: PMC3458737 DOI: 10.3762/bjoc.8.132

Abstract

The synthesis of diverse substituted indole structures on solid supports is described. The immobilization of nitrobenzoic acid onto Merrifield resin and the subsequent treatment with alkenyl Grignard reagents delivered indole carboxylates bound to solid supports. In contrast to results in the liquid phase, ortho,ortho-unsubstituted nitroarenes also delivered indole moieties in good yields. Subsequent palladium-catalyzed reactions (Suzuki, Heck, Sonogashira, Stille) delivered, after cleavage, the desired molecules in moderate to good yields over four steps. The scope and limitations are presented.

Keywords: Merrifield resin; chemical diversity; cross-coupling reactions; indole

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