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Issue 51, 2019
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Regioselective differentiation of vicinal methylene C–H bonds enabled by silver-catalysed nitrene transfer

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Abstract

Silver-catalyzed nitrene insertion enables the formation of benzosultams in good yield and with regioselectivity complementary to other transition metal nitrene-transfer catalysts. Preferential formation of six-membered benzosultam rings predominates for alkyl-substituted benzenesulphonamide precursors. Ligand-controlled tunability is also achieved for benzenesulphonamides with γ-branched alkyl substituents. Mechanistic probes suggest that the reaction pathway differs depending on whether a α (benzylic) or β (homobenzylic) C–H bond undergoes amidation, as well as the catalyst identity.

Graphical abstract: Regioselective differentiation of vicinal methylene C–H bonds enabled by silver-catalysed nitrene transfer

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Article information


Submitted
23 May 2019
Accepted
29 May 2019
First published
29 May 2019

Chem. Commun., 2019,55, 7362-7365
Article type
Communication
Author version available

Regioselective differentiation of vicinal methylene C–H bonds enabled by silver-catalysed nitrene transfer

R. J. Scamp, B. Scheffer and J. M. Schomaker, Chem. Commun., 2019, 55, 7362
DOI: 10.1039/C9CC04006D

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