Click with a boronic acid handle: a neighboring group-assisted click reaction that allows ready secondary functionalization.
The feasibility of a neighboring boronic acid-facilitated facile condensation of an aldehyde is described. This reaction is bio-orthogonal, complete at room temperature within minutes, and suitable for bioconjugation chemistry. The boronic acid group serves the dual purpose of catalyzing the condensation reaction and being a handle for secondary functionalization.
Department of Chemistry and Center for Diagnostics and Therapeutics, Georgia State University, Atlanta, 30303-3965, Georgia, USA. wang@gsu.edu.
Alexander B
AB
Draganov
Ke
K
Wang
Jalisa
J
Holmes
Krishna
K
Damera
Danzhu
D
Wang
Chaofeng
C
Dai
Binghe
B
Wang
D001547:Benzaldehydes / Q000737:chemistry; D052160:Benzothiazoles / Q000138:chemical synthesis*; D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D057930:Click Chemistry; D003500:Cyclization; D008956:Models, Chemical
D001547:Benzaldehydes; D052160:Benzothiazoles; D001897:Boronic Acids