21081-92-5

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 98-86-2 acetophenone 
• 122-00-9 para-methylacetophenone 
• 99-02-5 3'-Chloroacetophenone 
• 100-06-1 1-(4-methoxyphenyl)ethanone 

Downstream Products

• 1636-34-6 2,3-diphenyl-2,3-butanediol 
• 2575-20-4 3,3-diphenylbutan-2-one 

Relevant academic research and scientific papers

Generation and Reaction of Samarium(II) Iodide Equivalent from Samarium and Chlorotrimethylsilane/Sodium Iodide System in Acetonitrile

Samarium(II) iodide equivalent was generated from metallic samarium and Me3SiCl/NaI reagent in acetonitrile under ambient conditions.Dehalogenation of α-halocarbonyl compounds and reductive coupling of ketones were successfully carried out by the use of the samarium(II) species, thus generated, in acetonitrile.

Polymer-mediated pinacol rearrangements

Both poly(3,4-ethylenedioxythiophene) and poly(pyrrole) mediate a pinacol rearrangement of 1,2-diols. The yields of ketone or aldehyde products are comparable to those observed for treatment with mineral acids or Lewis acids. The advantage of this protocol is a two-phase reaction medium in hydrocarbon solvents that allows facile recovery of the products by simple filtration of the polymer and removal of solvents. Both the polymer and the hydrocarbon solvent may be recovered and used in subsequent reactions. Georg Thieme Verlag Stuttgart · New York.

Reductive pinacol coupling of aromatic carbonyl compounds catalytic in chromium(II)

Reductive coupling of aromatic and heteroaromatic aldehydes and ketones bearing different functional groups to pinacols is effectively catalysed with 1-5 mol % of Cr(II) salts or chromocene in THF/DMF mixtures in the presence of manganese powder and trialkyl chlorosilanes. Excellent dl selectivity can be achieved albeit with lower yield using trialkylsilyl chlorides with bulky substituents.

New Generation Method for a Samarium(II) Equivalent: Me3SiX (X = Br and I)/Sm-Assisted Intermolecular Carbon-Carbon Bond Forming Reactions for Carbonyl Compounds

Samarium(II) species can be efficiently generated in situ from a reaction between elemental samarium and chlorotrimethylsilane (Me3SiCl)/sodium iodide (NaI) reagent or bromotrimethylsilane (Me3SiBr) in acetonitrile.The reductive coupling reaction of carbonyl compounds was achieved by the action of Sm(II) reagent thus generated from Sm/Me3SiCl/NaI or Sm/Me3SiBr to give the corresponding pinacol products in moderate to high yields.The samarium(II) reagent induced the intermolecular coupling reaction of α,β-unsaturated esters with carbonyl compounds or imines followed by intramolecular cyclization to form the corresponding γ-lactones or γ-lactams in moderate yields.The reaction of α-bromo esters with carbonyl compounds using the Sm(II) species, generated from the Sm/Me3SiX system, led to the corresponding β-hydroxy esters in 52-95percent yields.

Photoinduced Electron Transfer in Pinacol Cleavage with Quinones via Highly Labile Cation Radicals. Direct Comparison of Charge-Transfer Excitation and Photosensitization

Benzopinacol and related diphenylethane-like donors (D) form electron donor-acceptor (EDA) complexes with chloranil and similar benzoquinones (A), in which the deliberate irradiation of the charge-transfer absorption band (hνCT) leads to oxidative cleavage (retropinacol) via electron transfer.Photosensitization by excitation of the ?-?* band of chloranil and diffusive quenching also effects the C-C bond cleavage of the same donors.The photoefficiencies of both photochemical processes are quantitatively compared with respect to the lifetimes of the pinacol cation radicals (D+ radical), as determined by the competition from back electron transfer and diffusion.These photoinduced processes are considered in the context of electron-transfer for an equivalent thermal reaction which occurs in the dark with high-potential quinones and electron-rich pinacols.

Reductive Coupling of Carbonyl Compounds with Zinc and Trimethylchlorosilane To Produce O-Silylated Pinacols. Effect of Ultrasonic Waves

Trimethylchlorosilane reacts with carbonyl compounds in the presence of zinc to give O-silylated pinacols, vicinal bis(trimethylsiloxy)alkanes, in good yields via reductive dimerization.This is very mild route to bis(siloxy)alkanes, which are easily converted to pinacols or pinacolones in excellent yields.Electron-donating groups accelerate coupling while electron-withdrawing groups have an inhibiting effect.Cross-coupling reactions yield a mixture of bis(siloxy)alkanes.Ultrasonic irradiations of these reactions increases the yields up to 50percent compared to stirring at the same temperature.