SIMes

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SIMes, also called H2IMes, is a type of N-heterocyclic carbene (NHC). It is a white solid that dissolves in organic solvents. SIMes is used as a ligand in organometallic chemistry, where it binds to metals in catalysts to help reactions proceed. It is closely related to the more common IMes, but has a saturated backbone (the S in SIMes stands for saturated), which makes it a bit more flexible. This flexibility is useful in catalysts such as Grubbs II. SIMes is prepared by alkylating trimethylaniline with dibromoethane, then closing the ring and performing dehydrohalogenation.