Synfacts 2014; 10(11): 1191
DOI: 10.1055/s-0034-1379343
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Ketones from Carbon Dioxide and Organolithium or Grignard Reagents

Paul Knochel
Thomas Klatt
Wu J, Yang X, He Z, Mao X, Hatton TA, * Jamison TF. * Massachusetts Institute of Technology, Cambridge, USA
Continuous Flow Synthesis of Ketons from Carbon Dioxide and Organolithium or Grignard Reagents.

Angew. Chem. Int. Ed. 2014;
53: 8416-8420
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20. Oktober 2014 (online)



The authors report two complementary continuous flow systems using either stoichiometric amounts or an excess of CO2 for the preparation of ketones. Starting from organolithium or Grignard reagents, the described synthesis shows significant advantages over conventional batch conditions in suppressing undesired symmetric ketone and tertiary alcohol byproducts.



The observation that in this reaction organolithium reagents are more reactive in Et2O than in THF is unprecedented. Furthermore, by integrating an in-line generation of organolithium or organomagnesium species, a telescoped one-flow process capable of preparing ketones in a modular fashion from simple precursors has been established.