917604-44-5

Upstream product

• 75-15-0 carbon disulfide 
• 250285-32-6 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride 
• 244187-81-3 1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene 

Downstream Products

• 1174750-03-8 [RuCl(4-isopropyltoluene)(1,3-di(2,6-diisopropylphenyl)-imidazolium-2-dithiocarboxylate)]PF₆ 
• 1208934-61-5 [(triphenylphosphine)Au(S₂C-IDip)]PF₆ 
• 1404113-28-5 [Pd(C,N-C6H4CH2-NMe2)(S2C·(1,3-bis(2,6-diisopropylphenyl)-imidazol-2-ylidene))](hexafluorophosphate) 

Relevant academic research and scientific papers

Zwitterionic dithiocarboxylates derived from N-heterocyclic carbenes: Coordination to gold surfaces

The zwitterionic dithiocarboxylates 1+-CS2 --4+-CS2- were prepared by reacting the corresponding N-heterocyclic carbenes 1,3-bis(2,6-diisoproylphenyl)imidazol- 2-ylidene (1), 1,3-diisopropylimidazol-2-ylidene (2), 1,3-dibenzylimidazol-2- ylidene (3) and 1,3-diethylbenzimidazol-2-ylidene (4) with CS2. In the latter two cases, the corresponding N-heterocylic carbene was generated in situ. Compounds 2+-CS2--4+-CS 2- were structurally characterised by single-crystal X-ray diffraction studies. The chemisorption of these zwitterionic dithiocarboxylates on solid gold substrates was investigated in situ and in real time by optical second harmonic generation (SHG). The resulting thin films were exemplarily characterised by near-edge X-ray absorption fine structure (NEXAFS) spectroscopy and X-ray photoelectron spectroscopy (XPS) in the case of 1+-CS 2- and 2+-CS2-, revealing the formation of almost contamination-free self-assembled monolayers, which exhibit a remarkable degree of orientational order.

Synthesis of Azolium-2-dithiocarboxylate Zwitterions under Mild, Aerobic Conditions

Twelve imidazolium-, imidazolinium-, or benzimidazolium-2-dithiocarboxylate zwitterions with aliphatic or aromatic substituents on their nitrogen atoms, including four new unsymmetrical 1-alkyl-3-arylimidazolium derivatives, were obtained in high yields (62–96 %) upon reaction of azolium salts with CS2 and Cs2CO3 in acetonitrile at room temperature. Compared to the previous strategies devised for the synthesis of NHC?CS2 betaines, this novel procedure relied on an innocuous, weak base and could be applied under mild aerobic conditions. All the new compounds were fully characterized by various analytical techniques and the molecular structures of two of them were determined by XRD analysis. An associative mechanism involving the concerted reaction of the azolium salts with both CS2 and CO32? was tentatively proposed to account for the formation of the zwitterionic adducts without the intervention of free carbenes. This would explain the good results obtained with a weak inorganic base that lacks the strength needed to deprotonate the azolium salt substrates.

Continuous-Flow N-Heterocyclic Carbene Generation and Organocatalysis

Two methods were assessed for the generation of common N-heterocyclic carbenes (NHCs) from stable imidazol(in)ium precursors using convenient and straightforward continuous-flow setups with either a heterogeneous inorganic base (Cs2CO3 or K3PO4) or a homogeneous organic base (KN(SiMe3)2). In-line quenching with carbon disulfide revealed that the homogeneous strategy was most efficient for the preparation of a small library of NHCs. The generation of free nucleophilic carbenes was next telescoped with two benchmark NHC-catalyzed reactions; namely, the transesterification of vinyl acetate with benzyl alcohol and the amidation of N-Boc-glycine methyl ester with ethanolamine. Both organocatalytic transformations proceeded with total conversion and excellent yields were achieved after extraction, showcasing the first examples of continuous-flow organocatalysis with NHCs.

Assessing the potential of zwitterionic NHOCS2 adducts for probing the stereoelectronic parameters of N-heterocyclic carbenes

Five imidazol(in)ium-2-dithiocarboxylates bearing cyclo-hexyl, mesityl, or 2,6-diisopropylphenyl substituents on their nitrogen atoms were prepared from the corresponding N-heterocyclic carbenes (NHCs) by reaction with carbon disul-fide. They were charact