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Metallocarbenes are organometallic compounds that feature a carbon atom double-bonded to a metal atom. This M=C functional group is central to their reactivity and applications. The metal can be from a wide range of transition metals, including tungsten, molybdenum, ruthenium, and chromium, as well as main group elements. The carbon atom is typically bonded to two substituents, which can be alkyl groups, aryl groups, or heteroatoms. The electronic structure of the metal-carbon bond can vary, leading to different types of metallocarbenes, often classified as either Fischer (where the metal is electron-deficient and bonded to an electron-donating group like an alkoxy or amino group) or Schrock (where the metal is electron-rich and bonded to alkyl or aryl groups).

The synthesis of metallocarbenes often involves reacting metal halides or alkoxides with organolithium or Grignard reagents, followed by treatment with carbene precursors or through other specialized routes. Their chemical behavior is characterized by their ability to undergo a variety of transformations, including cycloadditions, rearrangements, and especially olefin metathesis. This latter reaction, catalyzed by certain metallocarbenes, has revolutionized organic synthesis, enabling the efficient formation and cleavage of carbon-carbon double bonds. Olefin metathesis, powered by metallocarbene catalysts, finds widespread use in the synthesis of polymers, pharmaceuticals, and fine chemicals.