959929-03-4

Upstream product

• 2344-70-9 1-phenyl-3-butanol 
• 2550-26-7 4-Phenyl-2-butanone 
• 143097-80-7 2-bromo-4-phenylbutane 
• 61836-03-1 (rac)-(4-phenylbutan-2-ylthio)benzene 
• 59456-20-1 (rac)-(3-iodobutyl)benzeze 
• 17494-61-0 ((3-phenylpropyl)sulfonyl)benzene 
• 74-88-4 methyl iodide 
• 95274-98-9 1-phenyl-3,3'-bis(phenylsulfonyl)butane 

Downstream Products

• 79399-24-9 (rac)-[(2-methyl-4-phenylbutan-2-yl)sulfonyl]-benzene 
• 4489-84-3 3-methyl-1-phenylbut-2-ene 
• 6683-51-8 2-methyl-4-phenyl-1-butene 
• 768-56-9 4-Phenylbut-1-ene 
• 104-51-8 1-butylbenzene 
• 1520-44-1 1,3-diphenylbutane 

Relevant academic research and scientific papers

Two-Step Protocol for Iodotrimethylsilane-Mediated Deoxy-Functionalization of Alcohols

We have developed a two-step protocol for iodotrimethylsilane-mediated deoxy-functionalization of primary and secondary alcohols to afford products containing a C?N, C?S, or C?O bond. In the first step the alcohol undergoes iodination with iodotrimethylsilane, and in the second, the iodine atom is replaced by a N, S, or O nucleophile. Compared with traditional Mitsunobu reaction, non-acidic pre-nucleophiles can be used, and the reaction proceeds with retention of configuration. This operationally simple, highly efficient protocol can be used for some natural products and small-molecule drugs containing hydroxy-group.

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.

Reductions of challenging organic substrates by a nickel complex of a noninnocent crown carbene ligand

The first crown-tetracarbene complex of Ni(II) has been prepared, and its crystal structure determined. The complex can be reduced by Na/Hg, with an uptake of two electrons. The reduced complex reductively cleaves arenesulfonamides, including those derived from secondary aliphatic amines, and effects Birch reduction of anthracenes as well as reductive cleavage of stilbene oxides. Computational studies show that the orbital that receives electrons upon reduction of the complex 2 is predominantly based on the crown carbene ligand and also that the HOMO of the parent complex 2 is based on the ligand.

Super-electron donors: Bis-pyridinylidene formation by base treatment of pyridinium salts

Deprotonation of bispyridinium salt 7b affords bispyridinylidene 10, a very powerful neutral organic two-electron donor [E1/2 (DMF) = -1.13 V vs Ag/AgCI/KCI (sat)], presumably via the pyridinylidene 8. Donor 10 reduces aryl iodides and bromides to aryl anions in excellent yield and also reductively cleaves selected phenylalkylsulfones very efficiently.

Reductive cleavage of sulfones and sulfonamides by a neutral organic super-electron-donor (S.E.D.) reagent

Sulfones and sulfonamides are reductively cleaved using the neutral and easily prepared organic electron-donor, bis-imidazolylidene 3. Copyright