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Newsletter Issue 53 Jun/Jul 2014

Scientific Updates' What's New in Process ChemistryScientific Update
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Amide Preparation from Alcohols and Amines

Dr Will Watson

This paper describes the development, optimisation, and scope of the coupling of alcohols and amines to form amides using ruthenium based catalysts, with 3-methyl-2-butanone used as “oxidant”.

Reviews on Hydrogenation

Dr John Knight

I rarely include articles from OPRD Journal in the Newsletter items since many of our readers most likely turn to OPRD as one of their primary journals.  Notwithstanding this, I have been doing some catching up recently and noted a couple of items which I feel warrant a special mention.

Benzylic Hydroxyl Cleavage with Trimethylsilyl Iodide

Dr John Knight

Looking at OPRD, as I scan through the various reaction schemes, some steps catch my attention, not least because I consider the mechanistic steps of reactions I don’t recognise.  While looking at the article by Yamagami et al (OPRD, 2014, 18, 437) I saw the cleavage of a benzylic hydroxyl using TMS-Cl/NaI in acetonitrile.

Mechanism of the Negishi Coupling – the Importance of Salt

Dr Will Watson

A recent paper from Mike Organ’s group at York University describes their work on the mechanism of the Negishi coupling and reveals some very important details, particularly about the transmetalation step (ArZnX → ArPdX).

Alternative Solvents - The Effect of Carbon Dioxide

Dr Will Watson

Two recent papers have covered developments in a variety of alternative solvent systems including supercritical fluids (SCFs), gas-expanded liquids (GXLs), organic-aqueous tunable solvents (OATS), water at elevated temperature (WET), reversible ionic liquids (RevIls), and switchable hydrophilicity solvents.

Hydrogen Atom Transfer to Deliver Thermodynamically Preferred Product

Dr John Knight

Heterogeneous catalytic hydrogenation is of course a much-used chemical reaction and very efficiently delivers product with high atom economy.  The chemo- and stereoselectivity has been studied many times over the years and is in general fairly predictable based on steric impediment and the ability of the substrate to approach the catalyst surface for hydrogen transfer.

Base-Promoted Aldimine Formation

Dr John Knight

J L G Ruano et al published the base-catalysed formation of aldimines (JACS, 2014, 136, 1082) wherein they use pyrrolidine or anthranilic acid as organocatalyst to promote the formation of the aldimines between aldehydes and sulfonamides, sulfinamides and primary amines.

Frustrated Lewis Pair Mediated Hydroamination of Acetylenes

Dr John Knight

I have previously mentioned the use of frustrated Lewis pairs (FLPs) for the activation of hydrogen to catalyse reduction, typically of imines to amines.


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