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Ethynyl-B(dan) in [3+2] Cycloaddition and Larock Indole Synthesis: Synthesis of Stable Boron-Containing Heteroaromatic Compounds.
Li, Jialun; Tanaka, Hideya; Imagawa, Taiki; Tsushima, Takumi; Nakamoto, Masaaki; Tan, Jiajing; Yoshida, Hiroto.
Afiliación
  • Li J; Graduate School of Advanced Science and Engineering, Hiroshima University, Higashi-Hiroshima, 739-8526, Japan.
  • Tanaka H; Graduate School of Advanced Science and Engineering, Hiroshima University, Higashi-Hiroshima, 739-8526, Japan.
  • Imagawa T; Graduate School of Advanced Science and Engineering, Hiroshima University, Higashi-Hiroshima, 739-8526, Japan.
  • Tsushima T; Graduate School of Advanced Science and Engineering, Hiroshima University, Higashi-Hiroshima, 739-8526, Japan.
  • Nakamoto M; Graduate School of Advanced Science and Engineering, Hiroshima University, Higashi-Hiroshima, 739-8526, Japan.
  • Tan J; College of Chemistry, Beijing University of Chemical Technology (BUCT), Beijing, 100029, China.
  • Yoshida H; Graduate School of Advanced Science and Engineering, Hiroshima University, Higashi-Hiroshima, 739-8526, Japan.
Chemistry ; 30(8): e202303403, 2024 Feb 07.
Article en En | MEDLINE | ID: mdl-38109084
ABSTRACT
The cycloaddition of nitrile oxides with ethynyl-B(dan) (dan=naphthalene-1,8-diaminato) allowed the facile preparation of diverse isoxazolyl-B(dan) compounds, all of which displayed excellent protodeborylation-resistant properties. The dan-installation on the boron center proves vital to the high stability of the products as well as the perfect regioselectivity arising from hydrogen bond-directed orientation in the cycloaddition. The diminished boron-Lewis acidity of ethynyl-B(dan) also renders it amenable to azide-alkyne cycloaddition, Larock indole synthesis and related heteroannulations. The obtained boron-containing triazole, indoles, benzofuran and indenone exhibit sufficient resistance toward protodeborylation. Despite the commonly accepted transmetalation-inactive property derived from the diminished Lewis acidity, the synthesized heteroaryl-B(dan) compound was still found to be convertible to the oligoarene via sequential Suzuki-Miyaura coupling.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Chemistry Asunto de la revista: QUIMICA Año: 2024 Tipo del documento: Article País de afiliación: Japón 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: Chemistry Asunto de la revista: QUIMICA Año: 2024 Tipo del documento: Article País de afiliación: Japón Pais de publicación: Alemania