Reductive N-alkylation of nitroarenes: a green approach for the N-alkylation of natural products

J Org Chem. 2012 May 18;77(10):4578-85. doi: 10.1021/jo300303d. Epub 2012 Apr 30.

Abstract

A simple, mild, cost-effective, and green approach for the reductive mono-N-alkylation of nitroarenes has been developed. HOAc/Zn are utilized as the reducing system together with a carbonyl compound as an alkyl source in methanol. Excellent yields were obtained with stoichiometric control of mono- over dialkylated products. Application to five complex natural products demonstrated the practical utility of the method.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkylation
  • Biological Products / chemistry*
  • Catalysis
  • Molecular Structure
  • Nitro Compounds / chemistry*

Substances

  • Biological Products
  • Nitro Compounds