Iridium-catalyzed X-H insertions of sulfoxonium ylides.
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.
Mangion
Ian K
IK
Department of Process Research, Merck and Co., Inc., P.O. Box 2000, Rahway, New Jersey 07065, USA. ian_mangion@merck.com
Nwamba
Ikenna K
IK
Shevlin
Michael
M
Huffman
Mark A
MA
D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D004952:Esters; D007495:Iridium / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry*; D007769:Lactams / Q000737:chemistry; D008697:Methane / Q000031:analogs & derivatives / Q000737:chemistry; D015394:Molecular Structure; D013454:Sulfoxides / Q000737:chemistry*
D004952:Esters; D007659:Ketones; D007769:Lactams; D013454:Sulfoxides; C030011:carbene; D007495:Iridium; D008697:Methane