A Mild, DNA-Compatible Nitro Reduction Using B 2(OH) 4

Org Lett. 2019 Apr 5;21(7):2194-2199. doi: 10.1021/acs.orglett.9b00497. Epub 2019 Mar 12.

Abstract

A hypodiboric acid system for the reduction of nitro groups on DNA-chemical conjugates has been developed. This transformation provided good to excellent yields of the reduced amine product for a variety of functionalized aromatic, heterocyclic, and aliphatic nitro compounds. DNA tolerance to reaction conditions, extension to decigram scale reductions, successful use in a DNA-encoded chemical library synthesis, and subsequent target selection are also described.

Publication types

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

MeSH terms

  • Amines / chemistry*
  • Boron Compounds / chemistry*
  • Catalysis
  • DNA / chemistry
  • DNA / metabolism*
  • Molecular Structure
  • Nitro Compounds / chemistry*

Substances

  • Amines
  • Boron Compounds
  • Nitro Compounds
  • DNA