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Extent

1 digital object.

Description

Motivated by the lack of mild and general methods for accessing mono(amino)carbenes, we have developed an approach based on the photolysis of thermally stable N-triftosyl amino hydrazonates with blue light. No additives or catalysts are necessary. The resulting transient aminocarbenes can be trapped by [2+1] cycloaddition and σ-bond insertion reactions.

Creation Date

• 2025-05 to 2026-02

Date Issued

• 2026

Authors

• Abdellaoui, Mehdi
• Yorkgitis, Patrick

Principal Investigator

• Bertrand, Guy

Funding

This work was supported by the NSF (CHE-2246948). This research was also supported in part by the W. M. Keck Foundation through computing resources at the W. M. Keck Laboratory for Integrated Biology.

Topics

• Carbene
• Diazo compounds Density Functional Theory (DFT)
• Domain: Chemical sciences
• Mechanism
• Organic chemistry

Format

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• data

Language

• English

Identifier

Identifier: Guy Bertrand: https://orcid.org/0000-0003-2623-2363

Identifier: Mehdi Abdellaoui: https://orcid.org/0000-0002-2719-2095

Identifier: Patrick Yorkgitis: https://orcid.org/0000-0002-5285-0184

Related Resources

Primary associated publication

• Yorkgitis, Patrick; Abdellaoui, Mehdi; Bertrand, Guy (2026). Generation of mono(amino)carbenes from N-triftosyl amino hydrazonates with blue light. Chemical Communications. https://doi.org/10.1039/D6CC01379A

Software

• Neese, F. Software update: The ORCA program system—Version 5.0. WIRES Comput. Molec. Sci. 2022, 12, e1606. https://doi.org/10.1002/wcms.1606

Related data

• Patrick Yorkgitis, Mehdi Abdellaoui, Guy Bertrand CCDC 2530033: Experimental Crystal Structure Determination, 2026, https://doi.org/10.5517/ccdc.csd.cc2qxpzb

Collection image

• Image credit: Patrick Yorkgitis. "Generation of mono(amino)carbenes with blue light from hydrazonate salts."