Stability and reactivity control of carbenoids: recent advances and perspectives.

Metal carbenoids such as lithium or Simmons-Smith-type reagents are widely used in organic synthesis, particularly in cyclopropanation and homologation reactions. These reagents are often highly reactive and thermally labile, thus limiting their isolation and hampering the development of new synthetic applications. Recent years however, have shown that by means of systematic stabilization a control of reactivity and the development of new applications is possible. This feature article documents recent developments in the control of carbenoid reactivity and stability and highlights structural and electronic properties as well as applications in main group element and transition metal chemistry.