Cyclic (Alkyl)(Amino)Carbenes (CAACs): Stable Carbenes on the Rise

CONSPECTUS: Carbenes are compounds that feature a divalent carbon atom with only six electrons in its valence shell. In the singlet state, they possess a lone pair of electrons and a vacant orbital and therefore exhibit Lewis acidic and Lewis basic properties, which explains their very high reactivity. Following the preparation by our group in 1988 of the first representative, a variety of stable carbenes are now available, the most popular being the cyclic diaminocarbenes. In this Account, we discuss another class of stable cyclic carbenes, namely, cyclic (alkyl)(amino)carbenes (CAACs), in which one of the electronegative and π-donor amino substituents of diaminocarbenes is replaced by a σ-donating but not…

• CA
  Civil Aviation Administration of China
• OO
  Office of Science

  Award: DE-FG02-13ER16370
• DO
  Division of Chemistry

  Award: CHE-1359809