Author, as appears in the article.: Rodriguez, Manuel R.; Besora, Maria; Molina, Francisco; Maseras, Feliu; Mar Diaz-Requejo, M.; Perez, Pedro J.;

Department: Química Física i Inorgànica

URV's Author/s: Besora Bonet, Maria

Keywords: Singlet Regio Chemistry Carbethoxynitrene C-h Bonds Aziridination Amination

Abstract: Under silver catalysis conditions, using [Tp*Ag-,Ag-Br](2) as the catalyst precursor, allenes react with PhI=NTs in the first example of efficient metal-mediated intermolecular nitrene transfer to such substrates. The nature of the substituent at the allene seems crucial for the reaction outcome since arylallenes are converted into azetidine derivatives, whereas methylene aziridines are the products resulting from alkylallenes. Mechanistic studies allow proposing that azetidines are formed through unstable cyclopropylimine intermediates, which further incorporate a second nitrene group, both processes being silver-mediated. Methylene aziridines from alkylallenes derive from catalytic nitrene addition to the allene double bonds. Both routes have resulted to be productive for further synthetic transformations affording aminocyclopropanes.

Thematic Areas: Química Materiais Interdisciplinar General chemistry Farmacia Engenharias iv Engenharias iii Engenharias ii Colloid and surface chemistry Ciências biológicas ii Ciências biológicas i Ciências agrárias i Ciência de alimentos Chemistry, multidisciplinary Chemistry (miscellaneous) Chemistry (all) Chemistry Catalysis Biochemistry Astronomia / física

licence for use: https://creativecommons.org/licenses/by/3.0/es/

ISSN: 00027863

Author's mail: maria.besora@urv.cat

Author identifier: 0000-0002-6656-5827

Record's date: 2023-02-19

Papper version: info:eu-repo/semantics/acceptedVersion

Link to the original source: https://pubs.acs.org/doi/10.1021/jacs.0c04395

Licence document URL: http://repositori.urv.cat/ca/proteccio-de-dades/

Papper original source: Journal Of The American Chemical Society. 142 (30): 13062-13071

APA: Rodriguez, Manuel R.; Besora, Maria; Molina, Francisco; Maseras, Feliu; Mar Diaz-Requejo, M.; Perez, Pedro J.; (2020). Intermolecular Allene Functionalization by Silver-Nitrene Catalysis. Journal Of The American Chemical Society, 142(30), 13062-13071. DOI: 10.1021/jacs.0c04395

Article's DOI: 10.1021/jacs.0c04395

Entity: Universitat Rovira i Virgili

Journal publication year: 2020

Publication Type: Journal Publications