Tsuritani, Takayuki published the artcileTiCl4-n-Bu4NI as a Reducing Reagent: Pinacol Coupling and Enolate Formation from α-Halo Ketones, Computed Properties of 31253-08-4, the publication is Journal of Organic Chemistry (2000), 65(16), 5066-5068, database is CAplus and MEDLINE.
Reduction systems based on TiCl4/Bu4NI or NbCl5/Bu4NI combinations were found. Reduction of aromatic aldehydes or α-halo ketones by this reagent can be performed easily without using any other reducing agent. Thus, pinacol coupling of aromatic aldehydes, e.g. PhCHO, was efficiently promoted by TiCl4/Bu4NI or by NbCl5/Bu4NI in CH2Cl2/hexane to give corresponding 1,2-diol derivatives, e.g. dl-PhCH(OH)CH(OH)Ph, with high dl-stereoselectivities and in excellent yields. Addition of hexane and the reaction temperature were crucial for the enhanced dl-stereoselectivity. The pinacol coupling of aromatic ketones, e.g. acetophenone, provided corresponding diols, e.g. dl-PhCMe(OH)CMe(OH)Ph, with high dl-stereoselectivities, although in modest to poor yields. Aliphatic aldehydes did not provide desired diols under the reaction conditions, and the main product was an aldol condensation product. Reductive coupling of α-halo ketones and α-halo esters with PhCHO and heptanal was also investigated. For example, the reaction of PhCOCHIMe, with PhCHO in presence of TiCl4/Bu4NI gave mixed aldol-type condensation product PhCOCHMeCH(OH)Ph in 81% yield with high syn-stereoselectivity.
Journal of Organic Chemistry published new progress about 31253-08-4. 31253-08-4 belongs to iodides-buliding-blocks, auxiliary class Iodide,Ester, name is Ethyl 2-Iodopropionate, and the molecular formula is C4H6BrFO2, Computed Properties of 31253-08-4.
Referemce:
https://en.wikipedia.org/wiki/Iodide,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com