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Metal-free coupling of saturated heterocyclic sulfonylhydrazones with boronic acids

SYNTHESIS Comments Off

Nov 132014

The coupling of aromatic moieties with saturated heterocyclic partners is currently an area of significant interest for the pharmaceutical industry. Herein, we present a procedure for the metal-free coupling of 4-, 5-, and 6-membered saturated heterocyclic p-methoxyphenyl (PMP) sulfonylhydrazones with aryl and heteroaromatic boronic acids. This procedure enables a simple, two-step synthesis of a range of functionalized sp2–sp3 linked bicyclic building blocks, including oxetanes, piperidines, and azetidines, from their parent ketones.

Metal-free coupling of saturated heterocyclic sulfonylhydrazones with boronic acids

D.M. Allwood, D.C. Blakemore, A.D. Brown, S.V. Ley, J. Org. Chem. 2014, 79, 328-338

http://pubs.acs.org/doi/abs/10.1021/jo402526z

Mild and selective heterogeneous catalytic hydration of nitriles to amides by flowing through manganese dioxide

SYNTHESIS Comments Off

Nov 132014

A sustainable flow chemistry process for the hydration of nitriles, whereby an aqueous solution of the nitrile is passed through a column containing commercially available amorphous manganese dioxide, has been developed. The product is obtained simply by concentration of the output stream without any other workup steps. The protocol described is rapid, robust, reliable, and scalable, and it has been applied to a broad range of substrates, showing a high level of chemical tolerance.

Mild and selective heterogeneous catalytic hydration of nitriles to amides by flowing through manganese dioxide

C. Battilocchio, J.M. Hawkins, S.V. Ley, Org. Lett. 2014, 16, 1060-1063

http://pubs.acs.org/doi/abs/10.1021/ol403591c

Continuous flow chemistry: a discovery tool for new chemical reactivity patterns

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Nov 132014

Continuous flow chemistry: a discovery tool for new chemical reactivity patterns

J. Hartwig, J.B. Metternich, N. Nikbin, A. Kirschning, S.V. Ley, Org. Bio. Chem. 2014, 12, 3611

http://pubs.rsc.org/en/Content/ArticleLanding/2014/OB/c4ob00662c#!divAbstract

Continuous flow chemistry as a process intensification tool is well known. However, its ability to enable chemists to perform reactions which are not possible in batch is less well studied or understood. Here we present an example, where a new reactivity pattern and extended reaction scope has been achieved by transferring a reaction from batch mode to flow. This new reactivity can be explained by suppressing back mixing and precise control of temperature in a flow reactor set up.