4.7 Article

Cp*Co(iii)-catalyzed N-alkylation of amines with secondary alcohols

Journal

ORGANIC CHEMISTRY FRONTIERS
Volume 6, Issue 6, Pages 852-857

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c8qo01389f

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Funding

  1. CEFIPRA [IF-5805-1]
  2. IITK
  3. PK Kelkar Young Faculty Award

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The hydrogen borrowing methodology is a well-known, environmentally benign method for the direct alkylation of amines and alcohols as it produces only water as a side product. However, the direct alkylation of amines with secondary alcohols using first-row transition metals is very challenging. We herein report for the first time Cp*Co(iii)-catalyzed direct N-alkylation of amines starting from secondary alcohols. The reaction tolerates a wide variety of functional groups, including various aryl amines and amides. Our preliminary mechanistic investigations and DFT calculations suggest that [Cp*CoI2] is an active species, that PCy3 stabilizes the high-valent hydride intermediate, and that the reaction indeed proceeds through hydrogen auto-transfer processes.

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