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Cp*Rh(III)-Catalyzed Regioselective C(sp3)–H Methylation of 8‑Methylquinolines with Organoborons

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journal contribution
posted on 20.12.2019, 14:44 by Rakesh Kumar, Ritika Sharma, Rohit Kumar, Upendra Sharma
Rh­(III)-catalyzed highly regioselective methylation of the unactivated C­(sp3)–H bond of 8-methylquinolines with bench stable organoboron reagents is described. A variety of substituted 8-methylquinolines provided the highly regioselective monomethylated products with potassium methyltrifluoroborates/methylboronic acid through primary C­(sp3)–H bond activation. Complete chemoselectivity and regioselectivity were observed in all cases as methylation at the C2 position or dimethylation of the C­(sp3)–H bond of 8-methylquinoline was not detected. The mechanistic study uncovered the fact that the reaction may proceed through the five-membered rhodacycle intermediate.