Abstract
Electron-deficient carbenic carbon of metal carbene reacts with a heteroatom bearing lone pair electrons to generate ylide species. Metal carbenes can be generated in transition metal-catalyzed reaction of diazo compounds. Transition metals most commonly used in this type of transformations are copper and rhodium. Most frequently encountered heteroatoms are oxygen, sulfur and nitrogen; the corresponding ylides are oxonium ylides, sulfonium ylides, ammonium ylides, carbonyl ylides, thiocarbonyl ylides and azomethine ylides. Free ylides or metal associated ylides thus generated are reactive intermediates and have diverse reactivities: three major reaction modes are [2,3]-sigmatropic rearrangement, [1,2]-shift, and 1,3-dipole cycloaddition. These reactions can occur in either inter- or intramolecular manner. This chapter summarizes the progress in this field over the past 20 years, with emphasis on synthetic application of the ylide formation and following transformations. Moreover, the catalytic asymmetric ylide reaction is an emerging area in this field and the status quo is reviewed in this chapter. Finally, the ylide-like species generated from nitrene or metal-complexed nitrene and subsequent reactions are summarized.
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