- Cyclic Ether Synthesis via Palladium-Catalyzed Directed Dehydrogenative Annulation at Unactivated Terminal Positions
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Here, a palladium-catalyzed functionalization of unactivated sp3 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 sp3 C-H activation/intramolecular SN2 pathway was proposed.
- Thompson, Samuel J.,Thach, Danny Q.,Dong, Guangbin
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supporting information
p. 11586 - 11589
(2015/09/28)
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- Chemistry of free cyclic vicinal tricarbonyl compounds ('1,2,3-triones'). Part 1. Reaction of diazomethane and its derivatives with 5,5-dimethylcyclohexane-1,2,3-trione (='oxo-dimedone') and related cyclohexane-1,2,3-triones
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Interactions of diazomethane and of its derivatives as typical nucleophiles with cyclic 1,2,3-triones as efficient electrophiles lead to different results: a) formation of oxiranes (C,O insertion under loss of N2), b) nucleophilic addition yiel
- Schank, Kurt,La Vecchia, Luigi,Lick, Carlo
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p. 2071 - 2088
(2007/10/03)
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