Enantioselective Copper-Catalyzed Electrophilic Dearomative Azidation of ß-Naphthols.

The first example of copper-catalyzed enantioselective dearomative azidation of ß-naphthols using a readily available N3-transfer reagent is reported. A series of 2-hydroxy-1-naphthamides bearing a complex N-substituent were converted to the corresponding products in high yields with up to 96% ee, and chiral 1-azido-2-hydroxy-1-naphthoates were obtained with up to 90% ee under mild reaction conditions. The azides could be further transformed into the corresponding 1,2,3-triazoles smoothly via "click" reaction.

Rhodium-Catalyzed Successive C-H Bond Functionalizations To Synthesize Complex Indenols Bearing a Benzofuran Unit.

An efficient rhodium-catalyzed redox-neutral annulations of N-phenoxyacetamides and ynones via successive double C-H bond activations has been developed. A series of novel and complex indenols bearing a benzofuran unit were generated with moderate to excellent regioselecetivities under mild conditions. Adding N-ethylcyclohexanamine (CyNHEt) could restrict the formation of the mono C-H bond activation byproduct, which is not the intermediate of the reaction demonstrated via the mechanistic investigations.

Synthesis of ß-Alkyl 2-Hydroxychalcones by Rhodium-Catalyzed Coupling of N-Phenoxyacetamides and Nonterminal Propargyl Alcohols.

An efficient rhodium-catalyzed coupling of N-phenoxyacetamides and nonterminal propargyl alcohols has been developed. A series of ß-Alkyl 2-hydroxychalcones bearing diverse functional groups were obtained with excellent regio- and stereoselectivity, and the desired chalcones could then be converted to triazole and chromene smoothly.