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Ruthenium-Catalyzed Oxygenative Transformation of Terminal Propargyl Alcohols to Metheyleneketenes via Allenylidene Intermedia-tes: Synthesis ofα,β-Unsaturated Carboxylic Acid Derivatives
Received date: 2020-08-24
Revised date: 2020-09-07
Online published: 2020-09-09
Supported by
the National Natural Science Foundation of China(21971215)
A ruthenium-catalyzed oxygenative transformation of terminal propargyl alcohols to metheyleneketenes via allenylidene intermediates has been developed for the synthesis of a variety of α, β-unsaturated carboxylic acid derivatives. Mechanistic study experiments disclosed that oxygen transfer from pyridine- N-oxide to ruthenium allenylidene generated from the reaction of catalyst CpRuCl(PPh3)2/NaBPh4 with terminal propargyl alcohol resulted in the formation of reactive methyleneketene intermediate, which was trapped into nucleophilic addition reactions to afford α, β-unsaturated product. This reaction offers an attractive complementary strategy to the traditional approach for the synthesis of this class of unsaturated compounds, but in a distinct mechanism, which provides a novel method for the transformation of propargylic alcohols. The metal allenylidene-to-methyleneketene transformation also represents a new mechanistic modality for metal allenylidene-mediated catalysis.
Key words： Keywords ruthenium; allenylidene; propargyl alcohol; oxygen-transfer; methyleneketene; ketene
Xinyu Wang , Qihuan Li , Tingbin Wen . Ruthenium-Catalyzed Oxygenative Transformation of Terminal Propargyl Alcohols to Metheyleneketenes via Allenylidene Intermedia-tes: Synthesis ofα,β-Unsaturated Carboxylic Acid Derivatives[J]. Chinese Journal of Organic Chemistry, 2021 , 41(1) : 284 -296 . DOI: 10.6023/cjoc202008044
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