RT Journal Article
T1 Intermolecular Allene Functionalization by Silver-Nitrene Catalysis
A1 Ramírez Rodríguez, Manuel
A1 Besora, María
A1 Molina González, Francisco
A1 Maseras, Feliu
A1 Díaz Requejo, María Mar
A1 Pérez Romero, Pedro José
AB Under silver catalysis conditions, using [Tp*,BrAg]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.
PB American Chemical Society
SN 0002-7863
SN 1520-5126 (electrónico)
YR 2020
FD 2020-06
LK http://hdl.handle.net/10272/19650
UL http://hdl.handle.net/10272/19650
LA eng
NO Rodríguez, M. R., Besora, M., Molina, F., Maseras, F., Díaz-Requejo, M. M., & Pérez, P. J. (2020). Intermolecular Allene Functionalization by Silver-Nitrene Catalysis. Journal of the American Chemical Society, 142(30), 13062–13071. https://doi.org/10.1021/jacs.0c04395
NO Support for this work was provided by the MINECO (CTQ2017-82893-C2-1-R, CTQ2017-87792-R and Red Intecat CTQ2016-81923-REDC) and Universidad de Huel va (PO FEDER 2014-2020-UHU-1254043). MR thanks MINECO for a predoctoral fellowship.
DS Repositorio Institucional de la Universidad de Huelva
RD 30 may 2026