Cyclic Ether Synthesis via Palladium-Catalyzed Directed Dehydrogenative Annulation at Unactivated Terminal Positions

Journal of the American Chemical Society
Samuel J ThompsonGuangbin Dong

Abstract

Here, a palladium-catalyzed functionalization of unactivated sp(3) C-H bonds with internal alcohol nucleophiles is described. Directed by an oxime-masked alcohol, annulation chemoselectively occurs at the β position, leading to a range of aliphatic cyclic ethers with four- to seven-membered rings. Tethered primary, secondary, and tertiary free hydroxyl groups can all react to give the corresponding cyclized products. In addition, benzyl and silyl protected alcohols can also be directly coupled. An sp(3) C-H activation/intramolecular SN2 pathway was proposed.

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Citations

Feb 9, 2017·Journal of the American Chemical Society·Qi-Liang YangTian-Sheng Mei
May 10, 2017·Organic Letters·Long YangGang Li
Jun 21, 2017·Organic & Biomolecular Chemistry·Zhuqing LiuZhengkun Yu
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