Microwave-mediated synthesis of an arylboronate library.
A series of arylboronates has been synthesized from the reaction of 2-(2-, (3-, or (4-(bromomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 1{1-3} respectively with a range of N-, S-, and O-nucleophiles, using microwave-mediated chemistry. For the synthesis of N- and S-substituted boronates, a supported base, PS-NMM, was employed, and many reactions were complete within 15 min. With O-nucleophiles, a mixture of tetrabutylammonium bromide, potassium carbonate, and sodium hydroxide was employed. The resulting aminomethyl, mercaptomethyl, or alkoxy-/phenoxymethyl-arylboronates were subjected to microwave-mediated Suzuki Miyaura coupling reactions to afford a range of biaryls in moderate to good yields. The X-ray structures of five boronates were determined.
University of Greenwich, Chatham, UK. j.spencer@gre.ac.uk
John
J
Spencer
Christine B
CB
Baltus
Hiren
H
Patel
Neil J
NJ
Press
Samantha K
SK
Callear
Louise
L
Male
Simon J
SJ
Coles
D001897:Boronic Acids / Q000138:chemical synthesis*; D008872:Microwaves; D015394:Molecular Structure; D014961:X-Ray Diffraction
D001897:Boronic Acids