4.8 Article

Deoxygenative CO2 conversions with triphenylborane and phenylsilane in the presence of secondary amines or nitrogen-containing aromatics

Journal

GREEN CHEMISTRY
Volume 24, Issue 6, Pages 2385-2390

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d1gc04599g

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Funding

  1. JSPS KAKENHI [20H02780]
  2. Yakumo Foundation for Environmental Science
  3. Cooperative Research Program of Institute for Catalysis, Hokkaido University [19A1003]
  4. Photoexcitonix Project at Hokkaido University
  5. MEXT project Integrating Research Consortium on Chemical Science
  6. Grants-in-Aid for Scientific Research [20H02780] Funding Source: KAKEN

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BPh3 catalyst enables the N-methylation of secondary amines and C-methylenation of N,N-dimethylanilines or 1-methylindoles in the presence of CO2 and PhSiH3 without solvent. Additionally, a cascade reaction from 1-methyl-2-oxindole to 3,3'-methylenebis(1-methylindole) was observed.
BPh3 catalyzed the N-methylation of secondary amines and the C-methylenation (methylene-bridge formation between aromatic rings) of N,N-dimethylanilines or 1-methylindoles in the presence of CO2 (1 atm) and PhSiH3 without solvent at 30-40 degrees C. A cascade reaction from 1-methyl-2-oxindole to 3,3 '-methylenebis(1-methylindole) via 1-methylindole also proceeded.

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