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One-Pot Sequential Catalytic Hydration of Alkynes and α-Alkylation with Alcohols for the Synthesis of α-Alkylated Ketones

Authors

  • Juan Ma,

    1. Key Laboratory for Soft Chemistry and Functional Materials, Ministry of Education, Nanjing University of Science and Technology, Nanjing 210094 (P. R. China), Fax: (+86) 25-84431939
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  • Nana Wang,

    1. Key Laboratory for Soft Chemistry and Functional Materials, Ministry of Education, Nanjing University of Science and Technology, Nanjing 210094 (P. R. China), Fax: (+86) 25-84431939
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  • Dr. Feng Li

    Corresponding author
    1. Key Laboratory for Soft Chemistry and Functional Materials, Ministry of Education, Nanjing University of Science and Technology, Nanjing 210094 (P. R. China), Fax: (+86) 25-84431939
    • Key Laboratory for Soft Chemistry and Functional Materials, Ministry of Education, Nanjing University of Science and Technology, Nanjing 210094 (P. R. China), Fax: (+86) 25-84431939===

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Abstract

A strategy for the synthesis of α-alkylated ketones via one-pot, sequential, catalytic hydration of alkynes and α-alkylation with alcohols was proposed and successfully accomplished. In the presence of chloro[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]gold(I) ([(IPr)AuCl])/silver triflate (AgOTf) and water, a series of alkynes are first hydrated to give the corresponding methyl ketones, which in turn are α-alkylated by adding pentamethylcyclopentadienyliridium(III) chloride ([Cp*IrCl2]2)/KOtBu and alcohols to the reaction mixture. Notably, this reaction is highly attractive because of easily available starting materials, high atom efficiency, good to excellent yields, and minimal consumption of chemicals and energy. The present research will also facilitate the development of one-pot, sequential, catalytic reactions based on “hydrogen autotransfer” (or “hydrogen-borrowing”) processes.

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