Click reactions and boronic acids: applications, issues, and potential solutions.
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.
Dai
Chaofeng
C
Department of Chemistry and Center for Biotechnology and Drug Design, Georgia State University, Atlanta, Georgia 30303, USA.
Cheng
Yunfeng
Y
Cui
Jianmei
J
Wang
Binghe
B
D000480:Alkynes / Q000737:chemistry; D001897:Boronic Acids / Q000737:chemistry*; D015392:Chemistry, Inorganic / Q000379:methods*; D003300:Copper / Q000737:chemistry; D004247:DNA / Q000737:chemistry; D013942:Thymine Nucleotides / Q000737:chemistry
D000480:Alkynes; D001897:Boronic Acids; D013942:Thymine Nucleotides; D003300:Copper; D004247:DNA; C024157:thymidine 5'-triphosphate