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Rhodium-catalyzed (5+1) annulations between 2-alkenylphenols and allenes: a practical entry to 2,2-disubstituted 2H-chromenes.
Angew Chem Int Ed Engl. 2015 Feb 16; 54(8):2374-7.AC

Abstract

Readily available alkenylphenols react with allenes under rhodium catalysis to provide valuable 2,2-disubstituted 2H-chromenes. The whole process, which involves the cleavage of one C-H bond of the alkenyl moiety and the participation of the allene as a one-carbon cycloaddition partner, can be considered a simple, versatile, and atom-economical (5+1) heteroannulation. The reaction tolerates a broad range of substituents both in the alkenylphenol and in the allene, and most probably proceeds through a mechanism involving a rhodium-catalyzed C-C coupling followed by two sequential pericyclic processes.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Casanova N
Centro Singular de Investigación en Química Biolóxica e Materiais Moleculares (CIQUS) and Departamento de Química Orgánica 15782. Universidade de Santiago de Compostela (Spain).
Seoane A
No affiliation info available
Mascareñas JL
No affiliation info available
Gulías M
No affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

25580565

Citation

Casanova, Noelia, et al. "Rhodium-catalyzed (5+1) Annulations Between 2-alkenylphenols and Allenes: a Practical Entry to 2,2-disubstituted 2H-chromenes." Angewandte Chemie (International Ed. in English), vol. 54, no. 8, 2015, pp. 2374-7.
Casanova N, Seoane A, Mascareñas JL, et al. Rhodium-catalyzed (5+1) annulations between 2-alkenylphenols and allenes: a practical entry to 2,2-disubstituted 2H-chromenes. Angew Chem Int Ed Engl. 2015;54(8):2374-7.
Casanova, N., Seoane, A., Mascareñas, J. L., & Gulías, M. (2015). Rhodium-catalyzed (5+1) annulations between 2-alkenylphenols and allenes: a practical entry to 2,2-disubstituted 2H-chromenes. Angewandte Chemie (International Ed. in English), 54(8), 2374-7. https://doi.org/10.1002/anie.201410350
Casanova N, et al. Rhodium-catalyzed (5+1) Annulations Between 2-alkenylphenols and Allenes: a Practical Entry to 2,2-disubstituted 2H-chromenes. Angew Chem Int Ed Engl. 2015 Feb 16;54(8):2374-7. PubMed PMID: 25580565.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Rhodium-catalyzed (5+1) annulations between 2-alkenylphenols and allenes: a practical entry to 2,2-disubstituted 2H-chromenes. AU - Casanova,Noelia, AU - Seoane,Andrés, AU - Mascareñas,José L, AU - Gulías,Moisés, Y1 - 2015/01/07/ PY - 2014/10/22/received PY - 2014/11/20/revised PY - 2015/1/13/entrez PY - 2015/1/13/pubmed PY - 2015/1/13/medline KW - CH activation KW - allenes KW - annulations KW - reaction mechanisms KW - rhodium SP - 2374 EP - 7 JF - Angewandte Chemie (International ed. in English) JO - Angew Chem Int Ed Engl VL - 54 IS - 8 N2 - Readily available alkenylphenols react with allenes under rhodium catalysis to provide valuable 2,2-disubstituted 2H-chromenes. The whole process, which involves the cleavage of one C-H bond of the alkenyl moiety and the participation of the allene as a one-carbon cycloaddition partner, can be considered a simple, versatile, and atom-economical (5+1) heteroannulation. The reaction tolerates a broad range of substituents both in the alkenylphenol and in the allene, and most probably proceeds through a mechanism involving a rhodium-catalyzed C-C coupling followed by two sequential pericyclic processes. SN - 1521-3773 UR - https://www.unboundmedicine.com/medline/citation/25580565/Rhodium_catalyzed__5+1__annulations_between_2_alkenylphenols_and_allenes:_a_practical_entry_to_22_disubstituted_2H_chromenes_ DB - PRIME DP - Unbound Medicine ER -