Ruthenium-Catalyzed Oxidative Amidation of Alkynes to Amides

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Org. Lett. 2019, 21, 5346-5350.pdf (201.69 KB)
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URI: http://hdl.handle.net/10347/23355
ISSN: 1523-7060
E-ISSN: 1523-7052
DOI: 10.1021/acs.orglett.9b01993

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2019

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American Chemical Society
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Abstract

Complex CpRuCl(PPh3)2 catalyzes reactions of terminal alkynes with 4-picoline N-oxide and primary and secondary amines to afford the corresponding amides. The reactions occur in chlorinated solvent and aqueous medium, showing applications in peptide chemistry. Stoichiometric studies reveal that the true catalysts of the processes are the vinylidene cations [CpRu(═C═CHR)(PPh3)2]+ which are oxidized to the Ru(η2-CO)-ketenes by the N-oxide. Finally, nucleophilic additions of primary and secondary amines to the free ketenes yield the corresponding amides.

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NOTICE: This is the peer reviewed version of the following article: Álvarez-Pérez, A., Esteruelas, M. A., Izquierdo, S., Varela, J. A., Saá, C. (2019). Ruthenium-Catalyzed Oxidative Amidation of Alkynes to Amides. Org. Lett., 21, 13, 5346-5350. [doi: 10.1021/acs.orglett.9b01993]. This article may be used for non-commercial purposes in accordance with American Chemical Society Terms and Conditions for self-archiving

Keywords

Alkynes| Amides| Oxidative Annulation| Ruthenium

Bibliographic citation

Álvarez-Pérez, A., Esteruelas, M. A., Izquierdo, S., Varela, J. A., Saá, C. (2019). Ruthenium-Catalyzed Oxidative Amidation of Alkynes to Amides. Org. Lett., 21, 13, 5346-5350

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This work has received financial support from MINECO (projects CTQ2014-59015R, CTQ2017-87939R, CTQ2017-82935-P and ORFEO-CINQA network CTQ2016-81797-REDC), the Xunta de Ga-licia (project GRC2014/032, ED431C 2018/04, Centro singular de in-vestigación de Galicia accreditation 2016–2019, ED431G/09), DGA (No.E06_17R) and the European Union (European Regional Develop-ment Fund - ERDF). A. A.-P. thanks Spanish MICINN for a predoctoral FPI fellowship

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Copyright © 2019 American Chemical Society. This article may be used for non-commercial purposes in accordance with American Chemical Society Terms and Conditions for self-archiving

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Centro de Investigación en Química Biolóxica e Materiais Moleculares (CiQUS)
Química Orgánica