Abstract
Rhodium(I)-catalyzed decarbonylative direct ortho-olefination of 6-arylpurines with readily available vinyl carboxylic acids has been developed using purine as a directing group. The catalytic system consisting of bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate ([Rh(COD)2]OTf) and pivalic anhydride ((tBuCO)2O) performed well to give the ortho-olefinated products in high yields with excellent regio- and stereoselectivities in the absence of any external oxidant. Various substituted vinyl carboxylic acids behaved as efficient olefination reagents under the reaction conditions, and broad functional group tolerance in both coupling partners was observed. The substrate variation studies revealed that the N1 atom of purine moiety is essential for chelation-assisted C−H bond activation. This catalytic process involves a decarbonylation step, and (tBuCO)2O activates the carboxylic acids through in situ formation of highly active anhydrides.
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