Empowering alcohols as carbonyl surrogates for Grignard-type reactions

Chen-Chen Li, Haining Wang, Malcolm M. Sim, Zihang Qiu, Zhang-Pei Chen, Rustam Z. Khaliullin and Chao-Jun Li ()
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Chen-Chen Li: McGill University
Haining Wang: McGill University
Malcolm M. Sim: McGill University
Zihang Qiu: McGill University
Zhang-Pei Chen: McGill University
Rustam Z. Khaliullin: McGill University
Chao-Jun Li: McGill University

Nature Communications, 2020, vol. 11, issue 1, 1-9

Abstract: Abstract The Grignard reaction is a fundamental tool for constructing C-C bonds. Although it is widely used in synthetic chemistry, it is normally applied in early stage functionalizations owing to poor functional group tolerance and less availability of carbonyls at late stages of molecular modifications. Herein, we report a Grignard-type reaction with alcohols as carbonyl surrogates by using a ruthenium(II) PNP-pincer complex as catalyst. This transformation proceeds via a carbonyl intermediate generated in situ from the dehydrogenation of alcohols, which is followed by a Grignard-type reaction with a hydrazone carbanion to form a C-C bond. The reaction conditions are mild and can tolerate a broad range of substrates. Moreover, no oxidant is involved during the entire transformation, with only H2 and N2 being generated as byproducts. This reaction opens up a new avenue for Grignard-type reactions by enabling the use of naturally abundant alcohols as starting materials without the need for pre-synthesizing carbonyls.

Date: 2020
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DOI: 10.1038/s41467-020-19857-9

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