Ruthenium-Catalyzed Tandem Carbene/Alkyne Metathesis/N-H insertion. Synthesis of Benzofused Six-Membered Azaheterocycles
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ISSN: 1523-7060
E-ISSN: 1523-7052
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American Chemical Society
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Abstract
Cp*RuCl-based catalyst enables the expedient access to a variety of benzofused six- membered azaheterocycles from unprotected o-alkynylanilines and trimethylsilyldiazomethane through an unprecedent tandem carbene/alkyne metathesis/N-H insertion reaction. The transformation takes place under mild reaction conditions (room temperature, < 15 min) and with excellent functional group tolerance. The synthetic utility of the final products and a mechanistic rationale are also discussed.
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NOTICE: This is the peer reviewed version of the following article: Padín, D., Varela, J. A., Saá, C. (2020). Ruthenium-Catalyzed Tandem Carbene/Alkyne Metathesis/N-H insertion. Synthesis of Benzofused Six-Membered Azaheterocycles. Org. Lett., 22, 7, 2621-2625. [doi: 10.1021/acs.orglett.0c00596]. 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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Padín, D., Varela, J. A., Saá, C. (2020). Ruthenium-Catalyzed Tandem Carbene/Alkyne Metathesis/N-H insertion. Synthesis of Benzofused Six-Membered Azaheterocycles. Org. Lett., 22, 7, 2621-2625
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https://doi.org/10.1021/acs.orglett.0c00596Sponsors
This work has received financial support from MINECO (project CTQ2017-87939R and ORFEO-CINQA network RED2018-102387-T), the Xunta de Galicia (project ED431C 2018/04 and Centro singular de investigación de Galicia accreditation 2019-2022, ED431G 2019/03) and the European Union (European Regional Development Fund – ERDF). D.P. thanks MEC for a predoctoral FPU fellowship (FPU15/02132)
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Copyright © 2020 American Chemical Society. This article may be used for non-commercial purposes in accordance with American Chemical Society Terms and Conditions for self-archiving