RT info:eu-repo/semantics/article
T1 One-pot photocatalytic transformation of indolines into 3-thiocyanate indoles with new Ir(iii) photosensitizers bearing β-carbolines
A1 Sanz Villafruela, Juan
A1 Martínez Alonso, Carmen
A1 Echevarría Poza, Igor
A1 Vaquero Gutiérrez, Mónica
A1 Carbayo Martín, Mª Aránzazu
A1 Fidalgo Zorrilla, Jairo
A1 Rodríguez, Ana M.
A1 Cuevas Vicario, José Vicente
A1 Lima, João C.
A1 Moro, Artur J.
A1 Manzano Manrique, Blanca Rosa
A1 Jalón Sotés, Félix Ángel
A1 Espino Ordóñez, Gustavo
K1 Photocatalysis
K1 Singlet oxygen
K1 Iridium(III) photocatalysts
K1 Thiocyanation of indoles
K1 Photooxidative dehydrogenation of indolines
K1 β-carbolines
K1 Química orgánica
K1 Chemistry, Organic
K1 Química física
K1 Chemistry, Physical and theoretical
AB Current societies demand sustainable synthetic procedures and accordingly the combination of two photocatalytic reactions in a one-pot process is a very appealing chemical tool. In the present work, we report on the development of new Ir(III) bis-cyclometallated photosensitizers with β-carboline ligands and disclose a simple and unprecedented photocatalytic one-pot two-step protocol for the chemoselective and C-3 regioselective oxidative thiocyanation of indolines to produce the corresponding 3-thiocyanato-indoles. The procedure is performed in THF at room temperature, in the presence of NH4SCN, O2 and the Ir(III) photocatalysts under blue light exposure. Moreover, this methodology combines important advantages such as an outstanding efficiency, based on good yields for low catalyst loadings, along with an excellent sustainability founded on the use of O2 as a green oxidant and light as the energy source. In addition, DFT studies have allowed a clear interpretation of the photophysical and electrochemical properties of the Ir(III) complexes and transient absorption experiments, along with other experimental proof, have demonstrated that the two photocatalytic processes are mediated by 1O2. Our results pave the way for future developments in the field of photocatalysis using Ir(III) biscyclometallated complexes as photosensitizers.
PB Royal Society of Chemistry
SN 2052-1553
YR 2021
FD 2021
LK https://hdl.handle.net/10259/11334
UL https://hdl.handle.net/10259/11334
LA eng
NO We gratefully acknowledge the financial support provided by the Spanish Ministerio de Ciencia, Innovación y Universidades (RTI2018-100709-B-C21, CTQ (QMC)-RED2018-102471-T and PID2019-111215RB-I00), Junta de Castilla y León (BU087G19, Grant BU263P18) and Junta de Comunidades de Castilla-La Mancha-FEDER (JCCM) (grant SBPLY/19/180501/000260). J. Fidalgo and I. Echevarría want to acknowledge their fellowships to both the European Social Fund (ESF) and Consejería de Educación de la Junta de Castilla y León and J. Sanz-Villafruela to a fellowship from the ESF and the Plan Propio of the University of Castilla-La Mancha. M. V. (Prof. B. García Group, University of Burgos) is grateful for the financial support received from the Consejería de Educación-Junta de Castilla y León-FEDER (BU042U16-BU305P18) for the postdoctoral grant. This research has made use of the high-performance computing resources of the Castilla y León Supercomputing Center (SCAYLE, https://www.scayle.es), financed by FEDER (Fondo Europeo de Desarrollo Regional).
DS Repositorio Institucional de la Universidad de Burgos
RD 17-abr-2026