Click reactions and boronic acids: applications, issues, and potential solutions

Molecules. 2010 Aug 23;15(8):5768-81. doi: 10.3390/molecules15085768.

Abstract

Boronic acids have been widely used in a wide range of organic reactions, in the preparation of sensors for carbohydrates, and as potential pharmaceutical agents. With the growing importance of click reactions, inevitably they are also applied to the synthesis of compounds containing the boronic acid moiety. However, such applications have unique problems. Chief among them is the issue of copper-mediated boronic acid degradation in copper-assisted [2,3]-cycloadditions involving an alkyne and an azido compound as the starting materials. This review summarizes recent developments, analyzes potential issues, and discusses known as well as possible solutions.

Publication types

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

MeSH terms

  • Alkynes / chemistry
  • Boronic Acids / chemistry*
  • Chemistry, Inorganic / methods*
  • Copper / chemistry
  • DNA / chemistry
  • Thymine Nucleotides / chemistry

Substances

  • Alkynes
  • Boronic Acids
  • Thymine Nucleotides
  • Copper
  • DNA
  • thymidine 5'-triphosphate