Rhodium and iridium NHC complexes from chiral NHC precursors: Synthesis, structure, transfer hydrogenation catalysis and method validation

Raúl R. Quiñonez-López; Sara A. Cortés-Llamas; J. Roberto Estrada-Flores; José G. Alvarado-Rodríguez; Oscar Blanco-Alonso; A. Aarón Peregrina-Lucano; Elvia Becerra-Martínez; I. Idalia Rangel-Salas

doi:10.1016/j.poly.2023.116371

Rhodium and iridium NHC complexes from chiral NHC precursors: Synthesis, structure, transfer hydrogenation catalysis and method validation

Raúl R. Quiñonez-López, Sara A. Cortés-Llamas, J. Roberto Estrada-Flores, José G. Alvarado-Rodríguez, Oscar Blanco-Alonso, A. Aarón Peregrina-Lucano, Elvia Becerra-Martínez, I. Idalia Rangel-Salas

Centro de Nanociencias y Micro y Nanotecnologías (CNMN)

Research output: Contribution to journal › Article › peer-review

Abstract

Heteroleptic [Rh^IIICp*(NHC)] and [Ir^IIICp*(NHC)] complexes bearing a N-amino acid functionality derived from imidazolium salts were synthesized and characterized by NMR, IR, HR-MS, and single-crystal X-ray diffraction. A discussion of the structure of the [RhCp*{κ²(C,O)–NHC}Cl] complex 3f as a pair of diastereomers is presented. Catalysts were assessed for the transfer hydrogenation (TH) of ketones in basic propan-2-ol, obtaining good yields for the reduction products. A chromatographic method applied for measurements of compounds in TH as analytes was validated. The Rh and Ir complexes described here offer an original approach in the development of catalysts based in classic NHC precursors.

Original language	English
Article number	116371
Journal	Polyhedron
Volume	236
DOIs	https://doi.org/10.1016/j.poly.2023.116371
State	Published - 15 May 2023

Keywords

NHC ligands
Rhodium and iridium complexes
Transfer hydrogenation catalysis

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10.1016/j.poly.2023.116371

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Quiñonez-López, R. R., Cortés-Llamas, S. A., Estrada-Flores, J. R., Alvarado-Rodríguez, J. G., Blanco-Alonso, O., Peregrina-Lucano, A. A., Becerra-Martínez, E., & Rangel-Salas, I. I. (2023). Rhodium and iridium NHC complexes from chiral NHC precursors: Synthesis, structure, transfer hydrogenation catalysis and method validation. Polyhedron, 236, Article 116371. https://doi.org/10.1016/j.poly.2023.116371

@article{d878e47628734057b7d1f05857b185fa,

title = "Rhodium and iridium NHC complexes from chiral NHC precursors: Synthesis, structure, transfer hydrogenation catalysis and method validation",

abstract = "Heteroleptic [RhIIICp*(NHC)] and [IrIIICp*(NHC)] complexes bearing a N-amino acid functionality derived from imidazolium salts were synthesized and characterized by NMR, IR, HR-MS, and single-crystal X-ray diffraction. A discussion of the structure of the [RhCp*{κ2(C,O)–NHC}Cl] complex 3f as a pair of diastereomers is presented. Catalysts were assessed for the transfer hydrogenation (TH) of ketones in basic propan-2-ol, obtaining good yields for the reduction products. A chromatographic method applied for measurements of compounds in TH as analytes was validated. The Rh and Ir complexes described here offer an original approach in the development of catalysts based in classic NHC precursors.",

keywords = "NHC ligands, Rhodium and iridium complexes, Transfer hydrogenation catalysis",

author = "Qui{\~n}onez-L{\'o}pez, {Ra{\'u}l R.} and Cort{\'e}s-Llamas, {Sara A.} and Estrada-Flores, {J. Roberto} and Alvarado-Rodr{\'i}guez, {Jos{\'e} G.} and Oscar Blanco-Alonso and Peregrina-Lucano, {A. Aar{\'o}n} and Elvia Becerra-Mart{\'i}nez and Rangel-Salas, {I. Idalia}",

note = "Publisher Copyright: {\textcopyright} 2023 Elsevier Ltd",

year = "2023",

month = may,

day = "15",

doi = "10.1016/j.poly.2023.116371",

language = "Ingl{\'e}s",

volume = "236",

journal = "Polyhedron",

issn = "0277-5387",

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Quiñonez-López, RR, Cortés-Llamas, SA, Estrada-Flores, JR, Alvarado-Rodríguez, JG, Blanco-Alonso, O, Peregrina-Lucano, AA, Becerra-Martínez, E & Rangel-Salas, II 2023, 'Rhodium and iridium NHC complexes from chiral NHC precursors: Synthesis, structure, transfer hydrogenation catalysis and method validation', Polyhedron, vol. 236, 116371. https://doi.org/10.1016/j.poly.2023.116371

TY - JOUR

T1 - Rhodium and iridium NHC complexes from chiral NHC precursors

T2 - Synthesis, structure, transfer hydrogenation catalysis and method validation

AU - Quiñonez-López, Raúl R.

AU - Cortés-Llamas, Sara A.

AU - Estrada-Flores, J. Roberto

AU - Alvarado-Rodríguez, José G.

AU - Blanco-Alonso, Oscar

AU - Peregrina-Lucano, A. Aarón

AU - Becerra-Martínez, Elvia

AU - Rangel-Salas, I. Idalia

PY - 2023/5/15

Y1 - 2023/5/15

N2 - Heteroleptic [RhIIICp*(NHC)] and [IrIIICp*(NHC)] complexes bearing a N-amino acid functionality derived from imidazolium salts were synthesized and characterized by NMR, IR, HR-MS, and single-crystal X-ray diffraction. A discussion of the structure of the [RhCp*{κ2(C,O)–NHC}Cl] complex 3f as a pair of diastereomers is presented. Catalysts were assessed for the transfer hydrogenation (TH) of ketones in basic propan-2-ol, obtaining good yields for the reduction products. A chromatographic method applied for measurements of compounds in TH as analytes was validated. The Rh and Ir complexes described here offer an original approach in the development of catalysts based in classic NHC precursors.

AB - Heteroleptic [RhIIICp*(NHC)] and [IrIIICp*(NHC)] complexes bearing a N-amino acid functionality derived from imidazolium salts were synthesized and characterized by NMR, IR, HR-MS, and single-crystal X-ray diffraction. A discussion of the structure of the [RhCp*{κ2(C,O)–NHC}Cl] complex 3f as a pair of diastereomers is presented. Catalysts were assessed for the transfer hydrogenation (TH) of ketones in basic propan-2-ol, obtaining good yields for the reduction products. A chromatographic method applied for measurements of compounds in TH as analytes was validated. The Rh and Ir complexes described here offer an original approach in the development of catalysts based in classic NHC precursors.

KW - NHC ligands

KW - Rhodium and iridium complexes

KW - Transfer hydrogenation catalysis

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U2 - 10.1016/j.poly.2023.116371

DO - 10.1016/j.poly.2023.116371

M3 - Artículo

AN - SCOPUS:85151857481

SN - 0277-5387

VL - 236

JO - Polyhedron

JF - Polyhedron

M1 - 116371

ER -

Rhodium and iridium NHC complexes from chiral NHC precursors: Synthesis, structure, transfer hydrogenation catalysis and method validation

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