Reevaluation of the 2-Nitrobenzyl protecting group for nitrogen containing compounds: An application of flow photochemistry

    Using the Vapourtec easy-Photochem flow chemistry system with the unique UV-150 continuous photochemical reactor researchers from Vertex Pharmaceuticals Inc in Boston, USA have developed an approach to the photochemical deprotection of 2-Nitrobenzyl protecting groups for a range of nitrogen containing compounds.

    The are many options available for nitrogen protecting groups but the use of UV irradiation as the sole source for deprotection allows the flexibility for a wide range of functionalities and other protecting group strategies to be present in a given substrate. The o-Nitrobenzyl protecting group being stable under a range of conditions including acid and base and its removal under mild condition makes it of high synthetic value to chemists.

    NitrobenzylProtectingGroup

    The use of this protecting group is uncommon outside of the protection of amides. This procedure expands its utility and was applied to a variety of substrates including indoles, indazoles, pyrazoles, and secondary amines. Significant improvements in yield, reaction time and scalability were observed over traditional batch photochemical conditions.

    Find out more Published papers

    View the full Tetrahedron Letters paper.

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