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Design of a Photoredox Catalyst that Enables the Direct Synthesis of Carbamate-Protected Primary Amines via Photoinduced, Copper-Catalyzed N-Alkylation Reactions of Unactivated Secondary Halides

Jun Myun Ahn, Jonas C. Peters* and Gregory C. Fu*

*Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States, Email: gcfucaltech.edu, jpeterscaltech.edu

J. M. Ahn, J. C. Peters, G. C. Fu, J. Am. Chem. Soc., 2017, 139, 18101-18106.

DOI: 10.1021/jacs.7b10907 (free Supporting Information)



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Abstract

A copper-based photoredox catalyst, bearing a tridentate carbazolide/bisphosphine ligand, that can be activated upon irradiation by blue LEDs, achieves the coupling of a range of primary carbamates with unactivated secondary alkyl bromides at room temperature.


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proposed mechanism



Copper-Catalyzed Alkylation of Aliphatic Amines Induced by Visible Light

C. D. Matier, J. Schwaben, J. C. Peteres, G. C. Fu, J. Am. Chem. Soc., 2017, 139, 17707-17710.


Key Words

protected primary amines, carbamates, tert-butyl carbamates


ID: J48-Y2017