96550-93-5

Upstream product

• 111-83-1 1-bromo-octane 
• 5535-48-8 PVS 
• 35812-29-4 O-octyl-S-methyl dithiocarbonate 
• 112-29-8 1-bromo dodecane 
• 873-55-2 sodium benzenesulfonate 
• 629-27-6 1-Iodooctane 
• 13910-18-4 (n-decylthio)benzene 
• 111-66-0 oct-1-ene 
• 111-87-5 octanol 

Downstream Products

• 642410-52-4 tert-butyl (2S)-2-[(benzyloxycarbonyl)amino]-5-oxo-6-(phenylsulfonyl)pentadecanoate 
• 642410-54-6 benzyl (1S)-1-[(1-tert-butyldimethylsilyl)oxymethyl]-4-oxo-5-(phenylsulfonyl)tetradecylcarbamate 
• 642410-53-5 benzyl (1S)-1-[(1-ethoxyethoxy)methyl]-4-oxo-5-(phenylsulfonyl)tetradecylcarbamate 
• 124-18-5 decane 
• 872-05-9 1-Decene 
• 104-72-3 decylbenzene 
• 642410-61-5 benzyl (1S)-1-[(1-tert-butyldimethylsilyl)oxymethyl]-4-oxotetradecylcarbamate 
• 642410-76-2 (2S,5S)-N-(benzyloxycarbonyl)-2-[(tert-butyldimethylsilyloxy)methyl]-5-decylpyrrolidine 
• 642410-81-9 (2S,5R)-N-(benzyloxycarbonyl)-2-[(tert-butyldimethylsilyloxy)methyl]-5-decylpyrrolidine 
• 642410-59-1 tert-butyl (2S)-2-[(benzyloxycarbonyl)amino]-5-oxopentadecanoate 
• 642410-60-4 benzyl (1S)-1-[(1-ethoxyethoxy)methyl]-4-oxotetradecylcarbamate 
• 642410-75-1 (2S,5S)-N-(benzyloxycarbonyl)-5-decyl-2-(hydroxymethyl)pyrrolidine 
• 642410-78-4 (2S,5R)-N-(benzyloxycarbonyl)-5-decyl-2-(hydroxymethyl)pyrrolidine 

Relevant academic research and scientific papers

Borohydride-mediated radical addition reactions of organic iodides to electron-deficient alkenes

Cyanoborohydrides are efficient reagents in the reductive addition reactions of alkyl iodides and electron-deficient olefins. In contrast to using tin reagents, the reaction took place chemoselectively at the carbon-iodine bond but not at the carbon-bromine or carbon-chlorine bond. The reaction system was successfully applied to three-component reactions, including radical carbonylation. The rate constant for the hydrogen abstraction of a primary alkyl radical from tetrabutylammonium cyanoborohydride was estimated to be 4 M-1 s-1 at 25 °C by a kinetic competition method. This value is 3 orders of magnitude smaller than that of tributyltin hydride.

Iron-catalyzed cross-coupling of unactivated secondary alkyl thio ethers and sulfones with aryl grignard reagents

The first systematic investigation of unactivated aliphatic sulfur compounds as electrophiles in transition-metal-catalyzed cross-coupling are described. Initial studies focused on discerning the structural and electronic features of the organosulfur substrate that enable the challenging oxidative addition to the C(sp3)-S bond. Through extensive optimization efforts, an Fe(acac)3-catalyzed cross-coupling of unactivated alkyl aryl thio ethers with aryl Grignard reagents was realized in which a nitrogen "directing group" on the S-aryl moiety of the thio ether served a critical role in facilitating the oxidative addition step. In addition, alkyl phenyl sulfones were found to be effective electrophiles in the Fe(acac) 3-catalyzed cross-coupling with aryl Grignard reagents. For the latter class of electrophile, a thorough assessment of the various reaction parameters revealed a dramatic enhancement in reaction efficiency with an excess of TMEDA (8.0 equiv). The optimized reaction protocol was used to evaluate the scope of the method with respect to both the organomagnesium nucleophile and sulfone electrophile.

Tetraaryldisilanes as a novel strategic radical reagent

Reactivity of 1,1,2,2-tetraaryldisilanes as a radical reagent in ethanol was studied in reduction of alkyl bromides, addition to olefins and alkylation onto heteroaromatic bases with alkyl bromides. The present organodisilanes showed moderate to good reactivities for these three types of radical reactions. Among some disilanes prepared, 1,1,2,2-tetraphenyldisilane is the most useful in view of its reactivity and ease of preparation.

1,1,2,2-tetraphenyldisilane as a diversified radical reagent

Reactivity of 1,1,2,2-tetraphenyldisilane as a radical reagent in ethanol was studied in reduction of alkyl bromides, addition to olefin and alkylation onto heteroaromatic bases with alkyl bromides. The present organodisilane showed moderate to good reactivities for these three types of radical reactions.

Copper-catalyzed allylic alkylations of alkylzirconium intermediates

Hydrozirconation of olefins followed by exposure of the resulting alkylzirconium species to catalytic CuCN in the presence of activated halides or phosphonates gives rise to products of aklkylation in good yields under mild conditions.

Microbial Oxidation of Alkyl Aryl Sulfides to the Corresponding Optically Active Sulfoxides

Incubation of alkyl aryl sulfides with growing cells of Corynebacterium equi IFO 3730 afforded the corresponding sulfoxides and sulfones.The selectivity for the formation of sulfoxides over sulfones was higher with sulfides which have shorter alkyl chains.When methyl sulfides were used as substrates, formation of the corresponding sulfones was completely suppressed.Sulfoxides were revealed to have 87-100percent optically purities as to the (R) absolute configuration by HPLC analysis.The culture conditions seriously influenced the yield of oxidation products.High conversion of sulfides was attained when the reaction was carried out with grow ing cells in the logarithmic phase, in medium containing hexadecane as the carbon and energy source.

ASYMMETRIC SYNTHESIS OF CHIRAL SULFOXIDES VIA MICROBIAL OXIDATION OF SULFIDES

Incubation of alkyl aryl and allyl aryl sulfides with growing cells of Corynebacterium equi IFO 3730 gave the corresponding optically active sulfoxides with high enantiomeric excess.