Introducing 1,3-enyne functionalization by nitrene transfer reaction

Anabel M. Rodríguez; Giuseppe Sciortino; Lidia Muñoz-Gutierrez; Francisco Molina; Feliu Maseras; M. Mar Díaz-Requejo; Pedro J. Pérez

doi:10.1016/j.checat.2023.100865

Introducing 1,3-enyne functionalization by nitrene transfer reaction

Anabel M. Rodríguez, Giuseppe Sciortino, Lidia Muñoz-Gutierrez, Francisco Molina, Feliu Maseras^*, M. Mar Díaz-Requejo^*, Pedro J. Pérez^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Article › Research › peer-review

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Abstract

In the context of carbon–nitrogen bond formation, metal-catalyzed nitrene transfer reactions constitute a powerful transformation. While many saturated and unsaturated substrates can be modified with this strategy, the incorporation of nitrene into enynes yet remains undescribed. Herein, we report the first example of this transformation, leading to the formation of propargyl aziridines or unsaturated sulfinamides, corresponding to the attack of a copper-nitrene intermediate onto the ene or yne sites. Density functional theory (DFT) studies have provided an explanation for this diverse reactivity, which is sustained on the interactions of the enyne substituent with the pyrazolyl rings of the trispyrazolylborate ancillary ligand of the catalyst.

Original language	English
Article number	100865
Number of pages	12
Journal	Chem Catalysis
Volume	4
Issue number	1
DOIs	https://doi.org/10.1016/j.checat.2023.100865
Publication status	Published - 18 Jan 2024

Keywords

aziridines
copper catalysis
enynes functionalization
nitrene transfer
SDG9: Industry, innovation, and infrastructure
sulfinamides

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10.1016/j.checat.2023.100865

https://ddd.uab.cat/record/288564

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title = "Introducing 1,3-enyne functionalization by nitrene transfer reaction",

abstract = "In the context of carbon–nitrogen bond formation, metal-catalyzed nitrene transfer reactions constitute a powerful transformation. While many saturated and unsaturated substrates can be modified with this strategy, the incorporation of nitrene into enynes yet remains undescribed. Herein, we report the first example of this transformation, leading to the formation of propargyl aziridines or unsaturated sulfinamides, corresponding to the attack of a copper-nitrene intermediate onto the ene or yne sites. Density functional theory (DFT) studies have provided an explanation for this diverse reactivity, which is sustained on the interactions of the enyne substituent with the pyrazolyl rings of the trispyrazolylborate ancillary ligand of the catalyst.",

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AU - Rodríguez, Anabel M.

AU - Sciortino, Giuseppe

AU - Muñoz-Gutierrez, Lidia

AU - Molina, Francisco

AU - Maseras, Feliu

AU - Díaz-Requejo, M. Mar

AU - Pérez, Pedro J.

PY - 2024/1/18

Y1 - 2024/1/18

N2 - In the context of carbon–nitrogen bond formation, metal-catalyzed nitrene transfer reactions constitute a powerful transformation. While many saturated and unsaturated substrates can be modified with this strategy, the incorporation of nitrene into enynes yet remains undescribed. Herein, we report the first example of this transformation, leading to the formation of propargyl aziridines or unsaturated sulfinamides, corresponding to the attack of a copper-nitrene intermediate onto the ene or yne sites. Density functional theory (DFT) studies have provided an explanation for this diverse reactivity, which is sustained on the interactions of the enyne substituent with the pyrazolyl rings of the trispyrazolylborate ancillary ligand of the catalyst.

AB - In the context of carbon–nitrogen bond formation, metal-catalyzed nitrene transfer reactions constitute a powerful transformation. While many saturated and unsaturated substrates can be modified with this strategy, the incorporation of nitrene into enynes yet remains undescribed. Herein, we report the first example of this transformation, leading to the formation of propargyl aziridines or unsaturated sulfinamides, corresponding to the attack of a copper-nitrene intermediate onto the ene or yne sites. Density functional theory (DFT) studies have provided an explanation for this diverse reactivity, which is sustained on the interactions of the enyne substituent with the pyrazolyl rings of the trispyrazolylborate ancillary ligand of the catalyst.

KW - aziridines

KW - copper catalysis

KW - enynes functionalization

KW - nitrene transfer

KW - SDG9: Industry, innovation, and infrastructure

KW - sulfinamides

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JO - Chem Catalysis

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Introducing 1,3-enyne functionalization by nitrene transfer reaction

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Keywords

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