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Rhodium-catalyzed addition of arylboronic acids to isatins: an entry to diversity in 3-aryl-3-hydroxyoxindoles.
Org Lett. 2006 Jun 22; 8(13):2715-8.OL

Abstract

[reaction: see text] A general method for the catalytic 1,2-addition of aryl and alkenyl boronic acids to isatins is described using a rhodium(I)/triphenylphosphite catalyst. The application of this transformation allows the synthesis of a variety of 3-aryl-3-hydroxyoxindole building blocks in high yields. An enantioselective version of this reaction using a rhodium(I)/phosphoramidite system is also presented.

Authors+Show Affiliations

Toullec PY
Department of Organic and Molecular Inorganic Chemistry, Stratingh Institute, University of Groningen, The Netherlands.
Jagt RB
No affiliation info available
de Vries JG
No affiliation info available
Feringa BL
No affiliation info available
Minnaard AJ
No affiliation info available

MeSH

Boronic AcidsCatalysisCombinatorial Chemistry TechniquesIndolesIsatinMolecular StructureRhodium

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

16774239

Citation

Toullec, Patrick Y., et al. "Rhodium-catalyzed Addition of Arylboronic Acids to Isatins: an Entry to Diversity in 3-aryl-3-hydroxyoxindoles." Organic Letters, vol. 8, no. 13, 2006, pp. 2715-8.
Toullec PY, Jagt RB, de Vries JG, et al. Rhodium-catalyzed addition of arylboronic acids to isatins: an entry to diversity in 3-aryl-3-hydroxyoxindoles. Org Lett. 2006;8(13):2715-8.
Toullec, P. Y., Jagt, R. B., de Vries, J. G., Feringa, B. L., & Minnaard, A. J. (2006). Rhodium-catalyzed addition of arylboronic acids to isatins: an entry to diversity in 3-aryl-3-hydroxyoxindoles. Organic Letters, 8(13), 2715-8.
Toullec PY, et al. Rhodium-catalyzed Addition of Arylboronic Acids to Isatins: an Entry to Diversity in 3-aryl-3-hydroxyoxindoles. Org Lett. 2006 Jun 22;8(13):2715-8. PubMed PMID: 16774239.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Rhodium-catalyzed addition of arylboronic acids to isatins: an entry to diversity in 3-aryl-3-hydroxyoxindoles. AU - Toullec,Patrick Y, AU - Jagt,Richard B C, AU - de Vries,Johannes G, AU - Feringa,Ben L, AU - Minnaard,Adriaan J, PY - 2006/6/16/pubmed PY - 2007/4/17/medline PY - 2006/6/16/entrez SP - 2715 EP - 8 JF - Organic letters JO - Org Lett VL - 8 IS - 13 N2 - [reaction: see text] A general method for the catalytic 1,2-addition of aryl and alkenyl boronic acids to isatins is described using a rhodium(I)/triphenylphosphite catalyst. The application of this transformation allows the synthesis of a variety of 3-aryl-3-hydroxyoxindole building blocks in high yields. An enantioselective version of this reaction using a rhodium(I)/phosphoramidite system is also presented. SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/16774239/Rhodium_catalyzed_addition_of_arylboronic_acids_to_isatins:_an_entry_to_diversity_in_3_aryl_3_hydroxyoxindoles_ DB - PRIME DP - Unbound Medicine ER -