Selective control of secondary alcohols upgrading using Ir-catalyzed cross-coupling strategy
Science China Chemistry(2023)
摘要
The selective coupling of alcohols is a fascinating yet challenging approach for upgrading alcohols. Herein, we accomplished the controlled production of β-disubstituted ketones or upgraded secondary alcohols via the Ir-catalyzed cross-coupling of secondary alcohols in excellent yields with broad substrate scopes. This selective control was achieved by using an in-situ generated mono-NHC-Ir or a tris-NHC-Ir complex as the catalysts, respectively. Mechanistic studies reavealed that the delicate balance between dehydrogenation and hydrogenation abilities of these bifunctional catalysts is crucial for achieving different selectivity. The tris-NHC-Ir complex effectively facilitated dehydrogenation of alcohols and hydrogenation of intermediates, leading to the desired upgraded secondary alcohols. Conversely, the high dehydrogenation ability of the mono-NHC-Ir complex promoted the conversion of formed secondary alcohols back to ketones.
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关键词
cross-coupling,hydrogen-borrowing,NHC-Ir complexes,selectivity control,upgrading of alcohols
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