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Chem Soc Rev. 2007 Jul;36(7):1069-84. Epub 2007 Mar 1.

Direct sp3 C-H bond activation adjacent to nitrogen in heterocycles.

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  • 1Department of Process Research, Merck & Co., P.O. Box 2000, Rahway, NJ 07065, USA.


Activation of sp(3) C-H bonds adjacent to nitrogen in heterocycles is an attractive transformation that is emerging as a practical method in organic synthesis. This tutorial review aims to summarize the key examples of direct functionalization of nitrogen-containing heterocycles via metal-mediated and metal-catalyzed processes, which is meant to serve as a foundation for future investigations into this rapidly developing area of research. The review covers functionalization of N-heterocycles via alpha-lithiation with alkyllithium/diamine complexes, alpha-amino radical formation, metal-catalyzed direct C-H activation, C-H oxidations and oxidative couplings, and metal-catalyzed carbene insertions.

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