Reevaluation of the 2-nitrobenzyl protecting group for nitrogen containing compounds: an application of flow photochemistry
- Chloe I. Wendell, Michael J. Boyd
- Vertex Pharmaceuticals Inc., 50 Northern Avenue, Boston, MA, United StatesRead the publication that featured this abstract
Photochemistry under continuous flow conditions has many potential benefits for photochemical reactions that are problematic in batch. The 2-nitrobenzyl moiety is a photolabile protecting group for nitrogen. However, N-deprotection is generally impractical and, therefore, has not been extensively adopted. This Letter reports significant improvements in the N-deprotection of the 2-nitrobenzyl group through the application of continuous flow photolysis. This procedure was applied to a variety of substrates including indoles, indazoles, pyrazoles and secondary amines. Significant improvement in yield, reaction time and scalability was observed under continuous flow conditions.
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