Reevaluation of the 2-nitrobenzyl protecting group for nitrogen containing compounds: an application of flow photochemistry. Issue 7 (11th February 2015)

• Record Type: Journal Article
• Authors: Wendell, Chloe I.; Boyd, Michael J.
• Is Part Of: Tetrahedron letters. Volume 56:Issue 7(2015)
• Page Start: 897
• Page End: 899
• Publication Date: 2015-02-11
• Subjects: Photochemistry -- Flow -- Protecting group -- o-Nitrobenzyl; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.01.007
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: 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.