Pyridine wingtip in ▫$[Pd(Py-tzNHC)_2]^{2+}$▫ complex is a proton shuttle in the catalytic hydroamination of alkynes

Virant, Miha (author), Mihelač, Mateja (author), Gazvoda, Martin (author), Cotman, Andrej Emanuel (author), Frantar, Anja (author), Pinter, Balazs (author), Košmrlj, Janez (author)

The cationic palladium(II) complex 1 of pyridylmesoionic carbene ligand catalyzes Markovnikov-selective intermolecular hydroamination between anilines and terminal alkynes into the corresponding imines. The reaction proceeds at room temperature, in the absence of additives, with exquisite selectivity and diverse functional group tolerance. The key intrinsic feature of the catalyst is the pyridine wingtip confined to the proximity of the alkynophilic metal active site, which mimics the function of enzyme-like architectures by assisting entropically favored proton transfers.

• Language: English
• Keywords: catalysis, palladium, hydroamination, metal-ligand cooperation, proton transfer, DFT, hydrocarbons, chemical reactions, reaction mechanisms, metals, pyridines
• Work type: Article
• Typology: 1.01 - Original Scientific Article
• Organization: FKKT - Faculty of Chemistry and Chemical Technology
• Publication status: Published
• Publication version: Version of Record
• Year: 2020
• Number of pages: Str. 2157-2161
• Numbering: Vol. 22, iss. 6
• PID: 20.500.12556/RUL-125377
• UDC: 547.82:546.98
• ISSN on article: 1523-7060
• DOI: 10.1021/acs.orglett.0c00203
• COBISS.SI-ID: 1538522051
• Publication date in RUL: 12.03.2021

Record is a part of a journal

• Title: Organic letters
• Shortened title: Org. lett.
• Publisher: American Chemical Society
• ISSN: 1523-7060
• COBISS.SI-ID: 1916442

Licences

• License: CC BY 4.0, Creative Commons Attribution 4.0 International
• Link: http://creativecommons.org/licenses/by/4.0/
• Description: This is the standard Creative Commons license that gives others maximum freedom to do what they want with the work as long as they credit the author.
• Licensing start date: 12.03.2021

Secondary language

• Language: Slovenian
• Keywords: kataliza, paladij, hidroaminiranje, sodelovanje kovina-ligand, prenos protona, DFT, hidrokarbonati, kemijske reakcije, mehanizmi reakcij, kovine, piridini