Chem Sci Trans., 2012, 1(1), 9-12 Chemical Science Transactions DOI:10.7598/cst2012.119 ISSN: 2278-3458 Preparation and Application of 1, 1’-Bis-methyl-3, 3'- methylene-bisimidazolium Dicyanide as a Task-Specific Ionic liquid: An Efficient Catalyst in Benzoin Condensations SOHEIL SAYYAHI Chemistry Department, Mahshahr Branch, Islamic Azad University, Mahshahr 63519, Iran sayyahi.soheil@gmail.com Received 7 May 2012 / Accepted 16 May 2012 Abstract: A new ‘‘task-specific’’ ionic liquid (TSIL), 1, 1’-bis-methyl-3, 3’-methylene-bisimidazolium dicyanide has been prepared and used for the first time as the medium as well as catalyst for the synthesis of -hydroxy carbonyl group. Application of this ionic liquid in C–C bond formation reaction eliminates the use of the organic solvent, avoids the use of toxic materials, and allows the recovery and re-use of the catalyst. Keywords: Task-specific ionic liquid, C-C formation, Benzoin Condensation Introduction Ionic liquids (ILs) are commonly defined as substances composed only by ions which are liquid at or close to room temperature 1 . During the past years a growing number of scientists and engineers have investigated ionic liquids because of their outstanding advantages in several areas. Their unique physical properties and specific chemical behavior make these liquids very interesting for new and innovative applications 2 . Recently, researchers have discovered that ILs are more than just green solvents and they have found several applications such as replacing them with volatile organic solvents, making new materials, conducting heat effectively, supporting enzyme-catalyzed reactions, hosting a variety of catalysts, purification of gases, homogenous and heterogeneous catalysis, biological reactions media and removal of metal ions 3 . Benzoin type -hydroxy carbonyl group in general is important structural subunit in many biologically active compounds, industrial materials and is also important synthons for stereoselective syntheses of natural products, chiral auxiliaries and ligands 4 . Among the numerous synthetic strategies for introducing this moiety, the benzoin reaction and related additions remain perhaps, the most direct 5-9 . Several nucleophilic carbenes derived from heterocyclic compounds including triazolium, thiazole, triazole, imidazole 10, 11 and benzimidazolium salts are also employed as catalyst in benzoin condensation. Despite these developments, cyanide anion still remains a serious contender for practical synthesis of symmetrical acyloins, as evidenced by recent reports. Indeed, the development of novel cyanide ion catalytic systems has recently been RESEARCH ARTICLE