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. 2015 Apr 17;17(8):1938-41.
doi: 10.1021/acs.orglett.5b00641. Epub 2015 Mar 30.

Rh(III) and Ru(II)-catalyzed site-selective C-H alkynylation of quinolones

Dahye Kang  1   2 , Sungwoo Hong  1   2
Affiliations

Rh(III) and Ru(II)-catalyzed site-selective C-H alkynylation of quinolones

Dahye Kang et al. Org Lett. .

Abstract

C2- and C5-alkynylated quinolone scaffolds are core structures of numerous biologically active molecules. Utilizing TIPS-EBX as an alkynylating agent, we have developed an efficient and site-selective C5 alkynylation of 4-quinolones that is directed by the weakly coordinating carbonyl group. In addition, Ru(II) catalyzed C2-selective alkynylation was successfully realized via N-pyrimidyl group-directed cross-couplings to access valuable C2-alkynylated 4-quinolones. This strategy provides direct access to the C2 or C5 alkynylated 4-quinolones. Furthermore, the reaction was applied to isoquinolones for C3-selective alkynylation.

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