Hubei Collaborative Innovation Center for Advanced Chemical Materials, Ministry of Education Key Laboratory for the Synthesis and Application of Organic Functional Molecules, and College of Chemistry and Chemical Engineering , Hubei University , Wuhan 430062 , China.
Org Lett. 2018 Nov 16;20(22):7274-7277. doi: 10.1021/acs.orglett.8b03182. Epub 2018 Nov 2.
A weakly carboxylate-directed palladium(II)-catalyzed ortho-C-H alkynylation of diverse phenylacetic acids promoted by monoprotected amino acid ligand enabled is reported. The reaction has a broad substrate scope including α-secondary, tertiary, and quaternary phenylacetic acids. Notably, the direct ortho-C-H alkynylation of α-quaternary phenylacetic acids and chiral α-tertiary phenylacetic acids was achieved for the first time. Moreover, this method could be used for simple and efficient gram-scale synthesis and diversification of an anti-inflammatory drug.
本文报道了一种由单保护氨基酸配体促进的、弱羧酸导向的钯(II)催化的各种苯乙酸的邻位 C-H 炔基化反应。该反应具有广泛的底物范围，包括α-仲、叔和季苯乙酸。值得注意的是，首次实现了α-季苯乙酸和手性α-叔苯乙酸的直接邻位 C-H 炔基化。此外，该方法可用于简单高效的克级合成和抗炎药物的多样化。
