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Highly economical and direct amination of sp3 carbon using low-cost nickel pincer catalyst.
Brandt, Andrew; RanguMagar, Ambar B; Szwedo, Peter; Wayland, Hunter A; Parnell, Charlette M; Munshi, Pradip; Ghosh, Anindya.
Afiliação
  • Brandt A; Department of Chemistry, University of Arkansas at Little Rock 2801 South University Avenue Little Rock AR 72204 USA axghosh@ualr.edu +1 501 569 8838 +1 501 569 8827.
  • RanguMagar AB; Department of Chemistry, University of Arkansas at Little Rock 2801 South University Avenue Little Rock AR 72204 USA axghosh@ualr.edu +1 501 569 8838 +1 501 569 8827.
  • Szwedo P; Department of Chemistry, University of Arkansas at Little Rock 2801 South University Avenue Little Rock AR 72204 USA axghosh@ualr.edu +1 501 569 8838 +1 501 569 8827.
  • Wayland HA; Department of Chemistry, University of Arkansas at Little Rock 2801 South University Avenue Little Rock AR 72204 USA axghosh@ualr.edu +1 501 569 8838 +1 501 569 8827.
  • Parnell CM; Department of Chemistry, University of Arkansas at Little Rock 2801 South University Avenue Little Rock AR 72204 USA axghosh@ualr.edu +1 501 569 8838 +1 501 569 8827.
  • Munshi P; Research Center, Reliance Industries Limited Vadodara Gujarat 391346 India pradip.munshi@ril.com +91 265 261 6066.
  • Ghosh A; Department of Chemistry, University of Arkansas at Little Rock 2801 South University Avenue Little Rock AR 72204 USA axghosh@ualr.edu +1 501 569 8838 +1 501 569 8827.
RSC Adv ; 11(3): 1862-1874, 2021 Jan 04.
Article em En | MEDLINE | ID: mdl-35424101
ABSTRACT
Developing more efficient routes to achieve C-N bond coupling is of great importance to industries ranging from products in pharmaceuticals and fertilizers to biomedical technologies and next-generation electroactive materials. Over the past decade, improvements in catalyst design have moved synthesis away from expensive metals to newer inexpensive C-N cross-coupling approaches via direct amine alkylation. For the first time, we report the use of an amide-based nickel pincer catalyst (1) for direct alkylation of amines via activation of sp3 C-H bonds. The reaction was accomplished using a 0.2 mol% catalyst and no additional activating agents other than the base. Upon optimization, it was determined that the ideal reaction conditions involved solvent dimethyl sulfoxide at 110 °C for 3 h. The catalyst demonstrated excellent reactivity in the formation of various imines, intramolecularly cyclized amines, and substituted amines with a turnover number (TON) as high as 183. Depending on the base used for the reaction and the starting amines, the catalyst demonstrated high selectivity towards the product formation. The exploration into the mechanism and kinetics of the reaction pathway suggested the C-H activation as the rate-limiting step, with the reaction second-order overall, holding first-order behavior towards the catalyst and toluene substrate.

Texto completo: 1 Base de dados: MEDLINE Tipo de estudo: Health_economic_evaluation Idioma: En Ano de publicação: 2021 Tipo de documento: Article

Texto completo: 1 Base de dados: MEDLINE Tipo de estudo: Health_economic_evaluation Idioma: En Ano de publicação: 2021 Tipo de documento: Article