Facile Pd-catalyzed cross-coupling of 2'-deoxyguanosine O6-arylsulfonates with arylboronic acids.
[reaction: see text]. The O6-(2-mesitylenesulfonyl) derivative of 2'-deoxyguanosine undergoes a facile palladium-mediated C-C cross-coupling with arylboronic acids. Demonstrating the general applicability of this method, the synthesis of a previously undescribed class of 2-amino-6-arylpurine 2'-deoxynucleosides has been accomplished. The study also describes an evaluation of the O6-(2,4,6-triisopropylphenylsulfonyl) and the O6-(4-toluenesulfonyl) derivatives for the cross-coupling.
Lakshman
Mahesh K
MK
Department of Chemistry, City College of CUNY, 138th Street at Convent Avenue, New York, New York 10031-9198, USA. lakshman@sci.ccny.cuny.edu
Thomson
Paul F
PF
Nuqui
Mark A
MA
Hilmer
John H
JH
Sevova
Nonka
N
Boggess
Bill
B
D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D003849:Deoxyguanosine / Q000031:analogs & derivatives* / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*
D001897:Boronic Acids; D010165:Palladium; D003849:Deoxyguanosine