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Issue 13, 2017
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One-pot sustainable synthesis of tertiary alcohols by combining ruthenium-catalysed isomerisation of allylic alcohols and chemoselective addition of polar organometallic reagents in deep eutectic solvents

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Abstract

Ru(IV)-Catalysed redox isomerisation of allylic alcohols has, for the first time, been successfully assembled with the chemoselective addition of organolithium or organomagnesium reagents to the in situ formed ketones, en route to tertiary alcohols, employing deep eutectic solvents as environmentally friendly reaction media. The overall transformation, which formally involves three consecutive and different steps such as (i) the reduction of a C–C double bond, (ii) the oxidation of a secondary carbinol moiety, and (iii) a chemoselective C–C bond formation, takes place in protic and biorenewable eutectic mixtures in a sequential one-pot fashion using a commercially and easily available catalytic system, with excellent conversions (up to 99% yield), at room temperature and under air in the last step, with no concomitant reduction or enolisation processes, and with high atom economy, in agreement with the principles of the so-called green chemistry.

Graphical abstract: One-pot sustainable synthesis of tertiary alcohols by combining ruthenium-catalysed isomerisation of allylic alcohols and chemoselective addition of polar organometallic reagents in deep eutectic solvents

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Publication details

The article was received on 10 Feb 2017, accepted on 10 May 2017 and first published on 11 May 2017


Article type: Paper
DOI: 10.1039/C7GC00458C
Citation: Green Chem., 2017,19, 3069-3077
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    One-pot sustainable synthesis of tertiary alcohols by combining ruthenium-catalysed isomerisation of allylic alcohols and chemoselective addition of polar organometallic reagents in deep eutectic solvents

    L. Cicco, M. J. Rodríguez-Álvarez, F. M. Perna, J. García-Álvarez and V. Capriati, Green Chem., 2017, 19, 3069
    DOI: 10.1039/C7GC00458C

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