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Iridium-Catalyzed X-H Insertions of Sulfoxonium Ylides

Ian K. Mangion*, Ikenna K. Nwamba, Michael Shevlin and Mark A. Huffman

*Department of Process Research, Merck and Co., Inc., P.O. Box 2000, Rahway, New Jersey 07065, Email:

I. K. Mangion, I. K. Nwamba, M. Shevlin, M. A. Huffman, Org. Lett., 2009, 11, 3566-3569.

DOI: 10.1021/ol901298p

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A simple, commercially available iridium catalyst allows the use of sulfoxonium ylides as a carbene source for various intra- and intermolecular X-H bond insertions, including a practical ring-expansion strategy for lactams. The safety and stability of sulfoxonium ylides recommend them as preferable surrogates to traditional diazo ketones and esters.

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Key Words

α-Amination, N-Heterocycles

ID: J54-Y2009-2460