Reaction Optimization and Scale-Up of an Ethxycarbonylation
Reaction of Unprotected lodoindole with Carbonmonoxide Gas
This example illustrates the use of the new Vapourtec tube in tube gas reactor combined with the Vapourtec R-Series system to react reagent gases under pressure without the use of scale limiting pressure reactors (e.g. Parr ‘bombs’). Here we describe the catalytic ethoxycarbonylation of unprotected Iodoindole with CO Gas
It is well known that palladium catalysed C-C coupling reactions of aryl halides are a powerful tool in organic synthesis to functionalize aromatic rings but Pd catalysed carbonylations of aryl halides are relatively under used. There are very few examples at all of Pd-catalysed reactions of unprotected haloindoles probably due to the relatively acidic NH proton and the possibility of polymerisation under these conditions.
These reactions offer the specific, selective synthesis of a number of carboxylic acid derivatives accessing acids, esters, amides, aldehydes and ketones by reacting the aryl halide, CO and the corresponding nucleophile.
The use of carbon monoxide gas however requires a high level of safety precautions due to its toxicity and highly flammable nature and the use of specific volume limiting high pressure vessels. The application of flow chemistry to limit the reaction volume and the continuous replenishment of the reactants offers several advantages here as we are able to reduce the overall volume of CO in the system.
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