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Cp*Rh(III)-Catalyzed Regioselective C(sp 3)-H Methylation of 8-Methylquinolines with Organoborons

Cp*Rh(III)-Catalyzed Regioselective C(sp 3)-H Methylation of 8-Methylquinolines with Organoborons

Rakesh Kumar, Ritika Sharma, Rohit Kumar, Upendra Sharma

Org Lett. 2020 Jan 3;22(1):305-309.

PMID: 31859519

Abstract:

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP13862287	Potassium methyltrifluoroborate		13862-28-7	Price

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