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Iridium-Catalyzed X−H Insertions of Sulfoxonium Ylides

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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

Org. Lett., 2009, 11 (16), pp 3566–3569

DOI: 10.1021/ol901298p

Publication Date (Web): July 20, 2009

ian_mangion@merck.com

Section:

General Organic Chemistry

Abstract

The unique reactivity of sulfoxonium ylides as a carbene source is described for a variety of X−H bond insertions, taking advantage of a simple, commercially available iridium catalyst. This method has applications in both intra- and intermolecular reactivity, 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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This article has been cited by 2 ACS Journal articles (2 most recent appear below).

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Organic Letters2011 13 (20), 5480-5483
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Iridium(III) Catalyzed Diastereo- and Enantioselective C−H Bond Functionalization
Hidehiro Suematsu and Tsutomu Katsuki
Journal of the American Chemical Society2009 131 (40), 14218-14219
- Iridium(III) Catalyzed Diastereo- and Enantioselective C−H Bond Functionalization
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  Journal of the American Chemical Society2009 131 (40), 14218-14219
  Iridium(III)-salen complexes were found to efficiently catalyze the enantioselective C−H carbene insertion. The insertion reaction at the α-position of tetrahydrofuran or at the methylene of 1,4-cyclohexadiene proceeded with high enantio- (up to 99%) and ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links