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Copper-Catalyzed α-Arylation of Nitroalkanes with (Hetero)aryl Bromides/Iodides.
Huang, Jianqiang; Li, Taian; Lu, Xiaobiao; Ma, Dawei.
Afiliación
  • Huang J; Shenzhen Key Laboratory of Cross-Coupling Reactions, Southern University of Science and Technology (SUSTech), Department of Chemistry, Southern University of Science and Technology (SUSTech), Shenzhen, 518055, China.
  • Li T; Shenzhen Key Laboratory of Cross-Coupling Reactions, Southern University of Science and Technology (SUSTech), Department of Chemistry, Southern University of Science and Technology (SUSTech), Shenzhen, 518055, China.
  • Lu X; Shenzhen Key Laboratory of Cross-Coupling Reactions, Southern University of Science and Technology (SUSTech), Department of Chemistry, Southern University of Science and Technology (SUSTech), Shenzhen, 518055, China.
  • Ma D; Shenzhen Key Laboratory of Cross-Coupling Reactions, Southern University of Science and Technology (SUSTech), Department of Chemistry, Southern University of Science and Technology (SUSTech), Shenzhen, 518055, China.
Angew Chem Int Ed Engl ; 63(7): e202315994, 2024 Feb 12.
Article en En | MEDLINE | ID: mdl-38151905
ABSTRACT
α-Aryl substituted nitroalkanes are valuable synthetic building blocks that can be easily converted into α-aryl substituted aldehydes, ketones, carboxylic acids, as well as amines. Herein, an efficient Cu/oxalamide-catalyzed coupling between nitroalkanes and (hetero)aryl halides (Br, I) was developed to direct access highly diverse α-aryl substituted nitroalkanes. Compared with the current state of art, this protocol is more environmentally friendly and practical for synthetic chemists. This approach is characterized by a broad substrate scope on both nitroalkane part (primary nitroalkanes and nitromethane) and sp2 halide part ((hetero)aryl bromides/iodides and alkenyl bromides/iodides). The excellent functional group tolerance was observed, which would enable real world synthetic applications. More importantly, TON of current transformation reached to 3640, when some aryl iodides were used as coupling partners. This represents currently the highest catalyst turnover for transition-metal catalyzed α-arylation of nitroalkanes. Furthermore, the successful application in late-stage modification of complex molecules and synthesis of a known retinoid X receptor (RXR) antagonist exemplified its synthetic potential.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Angew Chem Int Ed Engl Año: 2024 Tipo del documento: Article País de afiliación: China Pais de publicación: Alemania
Texto completo
Añadir a Mi BVS
Imprimir
XML
PubMed Links
Buscar en Google

Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Angew Chem Int Ed Engl Año: 2024 Tipo del documento: Article País de afiliación: China Pais de publicación: Alemania