55563-70-7

Upstream product

• 100-58-3 phenylmagnesium bromide 
• 78643-42-2 5-bromopentanal dimethyl acetal 
• 36929-81-4 Tris-(4-brombutyl)-boran 
• 100-52-7 benzaldehyde 
• 20614-62-4 (1-hydroperoxycyclopentyl)benzene 
• 10487-96-4 1-phenylcyclopentanol 
• 4509-91-5 5-bromo-1-phenyl-1-pentanone 

Relevant academic research and scientific papers

Copper-catalyzed radical ring-opening halogenation with HX

An efficient copper-catalyzed radical ring-opening halogenation with HX (aq) is described. This protocol features redox-neutral conditions, green halogen sources, and a broad substrate scope, providing practical access to distally chlorinated, brominated and iodinated alkyl ketones and alkyl nitriles with moderate to good yields. This journal is

Enantioselective alkylation of aldehydes using functionalized alkylboron reagents catalyzed by a chiral titanium complex

A practical method is developed for the synthesis of enantioenriched functionalized secondary alcohols through catalytic enantioselective alkylation of aldehydes. Functionalized alkylboron reagents, [FG-(CH2) n]3B (FG = Br, TIPSO, PhtN, CO2iPr, and CN) prepared from terminal olefin precursors by hydroboration, undergo enantioselective addition to aldehydes in the presence of a catalytic amount (5 mol %) of 3-(3,5-diphenylphenyl)-H8-BINOL and excess titanium tetraisopropoxide to afford the corresponding functionalized alcohols in high enantioselectivities up to 99% ee.

Effects of phosphorus substituents on reactions of α- alkoxyphosphonium salts with nucleophiles

The effects of phosphorus substituents on the reactivity of α-alkoxyphosphonium salts with nucleophiles has been explored. Reactions of α-alkoxyphosphonium salts, prepared from various acetals and tris(o-tolyl)phosphine, with a variety of nucleophiles proceeded efficiently. These processes represent the first examples of high-yielding nucleophilic substitution reactions of α-alkoxyphosphonium salts. The reactivity of these salts was determined by a balance between steric and electronic factors, respectively, represented by cone angles θ and CO stretching frequencies ν (steric and electronic parameters, respectively). In addition, a novel reaction of α-alkoxyphosphonium salts derived from Ph3P with Grignard reagents was observed to take place in the presence of O2 to afford alcohols in good yields. A radical mechanism is proposed for this process that has gained support from isotope-labeling and radical-inhibition experiments. A dramatic change in the reactivity of an α-alkoxyphosphonium salt toward nucleophiles is observed due to the steric and electronic nature of the phosphine substituents. By changing the type of phosphorus substituents, the reaction pathway can be controlled to proceed selectively by substitution or a new radical reaction (see scheme; OTf=trifluoromethansulfonate, TMS=trimethylsilyl, o-tol=tolyl). Copyright

An unusual reaction of α-alkoxyphosphonium salts with Grignard reagents under an O2 atmosphere

An unusual and novel reaction of α-alkoxyphosphonium salts, generated from O,O-acetals and Ph3P, with Grignard reagents under an O 2 atmosphere afforded alcohols in moderate to high yields. It was clarified by isotopic labelling experiments that the reaction proceeded via a novel radical pathway.