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Rhodium-Catalyzed Annulation of ortho-Alkenyl Anilides with Alkynes: Formation of Unexpected Naphthalene Adducts.
Angew Chem Int Ed Engl. 2019 Feb 04; 58(6):1700-1704.AC

Abstract

o-Alkenyl N-triflylanilides underwent rhodium(III)-catalyzed oxidative annulations with alkynes to produce different types of naphthylamides in a process which involves the cleavage of two C-H bonds. Remarkably, besides formal dehydrogenative (4C+2C) cycloadducts, the reaction also produces variable amounts of isomeric naphthylamides, whose formation requires a formal migration of the alkenyl moiety from the ortho to the meta position of the anilide. The annulation reaction can be efficiently carried out in the absence of external oxidants, such as Cu(OAc)2 .

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Authors+Show Affiliations

Seoane A
Centro Singular de Investigación en Química Biolóxica e Materiais Moleculares (CIQUS) and Departamento de Química Orgánica, Universidade de Santiago de Compostela, 15782, Santiago de Compostela, Spain.
Comanescu C
Centro Singular de Investigación en Química Biolóxica e Materiais Moleculares (CIQUS) and Departamento de Química Orgánica, Universidade de Santiago de Compostela, 15782, Santiago de Compostela, Spain. National Institute of Materials Physics, Atomiştilor 405A, 077125, Măgurele-Ilfov, Romania.
Casanova N
Centro Singular de Investigación en Química Biolóxica e Materiais Moleculares (CIQUS) and Departamento de Química Orgánica, Universidade de Santiago de Compostela, 15782, Santiago de Compostela, Spain.
García-Fandiño R
Centro Singular de Investigación en Química Biolóxica e Materiais Moleculares (CIQUS) and Departamento de Química Orgánica, Universidade de Santiago de Compostela, 15782, Santiago de Compostela, Spain.
Diz X
Centro Singular de Investigación en Química Biolóxica e Materiais Moleculares (CIQUS) and Departamento de Química Orgánica, Universidade de Santiago de Compostela, 15782, Santiago de Compostela, Spain.
Mascareñas JL
Centro Singular de Investigación en Química Biolóxica e Materiais Moleculares (CIQUS) and Departamento de Química Orgánica, Universidade de Santiago de Compostela, 15782, Santiago de Compostela, Spain.
Gulías M
Centro Singular de Investigación en Química Biolóxica e Materiais Moleculares (CIQUS) and Departamento de Química Orgánica, Universidade de Santiago de Compostela, 15782, Santiago de Compostela, Spain.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

30507055

Citation

Seoane, Andrés, et al. "Rhodium-Catalyzed Annulation of ortho-Alkenyl Anilides With Alkynes: Formation of Unexpected Naphthalene Adducts." Angewandte Chemie (International Ed. in English), vol. 58, no. 6, 2019, pp. 1700-1704.
Seoane A, Comanescu C, Casanova N, et al. Rhodium-Catalyzed Annulation of ortho-Alkenyl Anilides with Alkynes: Formation of Unexpected Naphthalene Adducts. Angew Chem Int Ed Engl. 2019;58(6):1700-1704.
Seoane, A., Comanescu, C., Casanova, N., García-Fandiño, R., Diz, X., Mascareñas, J. L., & Gulías, M. (2019). Rhodium-Catalyzed Annulation of ortho-Alkenyl Anilides with Alkynes: Formation of Unexpected Naphthalene Adducts. Angewandte Chemie (International Ed. in English), 58(6), 1700-1704. https://doi.org/10.1002/anie.201811747
Seoane A, et al. Rhodium-Catalyzed Annulation of ortho-Alkenyl Anilides With Alkynes: Formation of Unexpected Naphthalene Adducts. Angew Chem Int Ed Engl. 2019 Feb 4;58(6):1700-1704. PubMed PMID: 30507055.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Rhodium-Catalyzed Annulation of ortho-Alkenyl Anilides with Alkynes: Formation of Unexpected Naphthalene Adducts. AU - Seoane,Andrés, AU - Comanescu,Cezar, AU - Casanova,Noelia, AU - García-Fandiño,Rebeca, AU - Diz,Xabier, AU - Mascareñas,José L, AU - Gulías,Moisés, Y1 - 2019/01/11/ PY - 2018/10/12/received PY - 2018/12/7/pubmed PY - 2018/12/7/medline PY - 2018/12/4/entrez KW - C−H activation KW - anilides KW - annulation KW - naphthylamines KW - rhodium SP - 1700 EP - 1704 JF - Angewandte Chemie (International ed. in English) JO - Angew Chem Int Ed Engl VL - 58 IS - 6 N2 - o-Alkenyl N-triflylanilides underwent rhodium(III)-catalyzed oxidative annulations with alkynes to produce different types of naphthylamides in a process which involves the cleavage of two C-H bonds. Remarkably, besides formal dehydrogenative (4C+2C) cycloadducts, the reaction also produces variable amounts of isomeric naphthylamides, whose formation requires a formal migration of the alkenyl moiety from the ortho to the meta position of the anilide. The annulation reaction can be efficiently carried out in the absence of external oxidants, such as Cu(OAc)2 . SN - 1521-3773 UR - https://www.unboundmedicine.com/medline/citation/30507055/Rhodium_Catalyzed_Annulation_of_ortho_Alkenyl_Anilides_with_Alkynes:_Formation_of_Unexpected_Naphthalene_Adducts_ DB - PRIME DP - Unbound Medicine ER -