876133-00-5

Upstream product

• 882-33-7 diphenyldisulfane 
• 612058-33-0 (1R)-(1-phenylethoxy)(diphenyl)phosphine 
• 155127-04-1 1-phenyl-1-(phenylthio)-1-(tributylstannyl)methane 
• 333-27-7 methyl trifluoromethanesulfonate 
• 108-98-5 thiophenol 
• 672-65-1 (1-chloroethyl)benzene 
• 100-68-5 methyl-phenyl-thioether 
• 102761-62-6 phosphoric acid tris-((R)-1-phenyl-ethyl ester) 
• 19342-01-9 (S)-N,N-dimethyl-1-phenylethylamine 
• 1517-69-7 (R)-1-phenylethanol 
• 1445-91-6 (S)-1-phenylethanol 
• 3111-52-2 potassium thiophenolate 

Relevant academic research and scientific papers

Regio- And Stereoselective (S N2) N -, O -, C - And S -Alkylation Using Trialkyl Phosphates

Bimolecular nucleophilic substitution (S N 2) is one of the most well-known fundamental reactions in organic chemistry to generate new molecules from two molecules. In principle, a nucleophile attacks from the back side of an alkylating agent having a suitable leaving group, most commonly a halide. However, alkyl halides are expensive, very harmful, toxic and not so stable, which makes them problematic for laboratory use. In contrast, trialkyl phosphates are inexpensive, readily accessible and stable at room temperature, under air, and are easy to handle, but rarely used as alkylating agents in organic synthesis. Here, we describe a mild, straightforward and powerful method for nucleophilic alkylation of various N -, O -, C - and S -nucleophiles using readily available trialkyl phosphates. The reaction proceeds smoothly in excellent yield, and quantitative yield in many cases, and covers a wide range of substrates. Further, the rare stereoselective transfer of secondary alkyl groups has been achieved with inversion of configuration of chiral centers (up to 98% ee).

Transition metal-free coupling reactions of benzylic trimethylammonium salts with di(hetero)aryl disulfides and diselenides

A new protocol was developed to synthesize (enantioenriched) thioethers and selenoethers from (chiral) benzylic trimethylammonium salts and di(hetero)aryl disulfides or diselenides. These syntheses were promoted by the presence of weak base and did not require the use of any transition metal, and resulted in the target products with good to excellent yields (72-94%). Using quaternary ammonium salts synthesized from enantiomerically enriched amines led to highly enantiopure benzylic thioethers and selenoethers (94-99% ee) with configurations reversed from those of their enantioenriched quaternary ammonium salts. This journal is

Stereospecific Nucleophilic Substitution of Enantioenriched Tertiary Benzylic Amines via in Situ Activation with Benzyne

A one-pot protocol has been developed for sequential benzyne activation and nucleophilic substitution of enantioenriched tertiary benzylic amines. In the presence of 2-(trimethylsilyl)phenyl triflate and CsF, a range of enantioenriched tertiary benzylic amines were substituted by various nucleophiles, delivering structurally diverse benzylic compounds in moderate to excellent yields with excellent retention of enantiopurity. Importantly, this operationally simple protocol permitted formation of various chiral C-S, C-Se, C-C, and C-N bonds with excellent enantiopurity under metal-free conditions.

Supercritical carbon dioxide: A promoter of carbon-halogen bond heterolysis

Amazing reaction medium: Supercritical carbon dioxide, with zero dipole moment, lower dielectric constant than pentane, and non-hydrogen-bonding behavior, ionizes carbon-halogen bonds, dissociates the resulting ion pairs, and escapes from capture by the carbocation intermediates at temperatures above 40 °C. These properties allow the observation of carbocation chemistry in the absence of acids.

A convenient method for the preparation of alkyl aryl sulfides from alcohols and (chloromethylene)dimethylammonium chloride

(Chloromethylene)dimethylammonium chloride (Vilsmeier reagent), prepared easily from DMF and oxalyl chloride, works as an efficient condensation reagent for the thioetherification of alcohols in one-pot under mild conditions. Various alcohols are successively converted into the corresponding sulfides with inversion of configurations in moderate to high yields. Copyright

A new method for the preparation of alkyl aryl sulfides from alcohols via alkoxydiphenylphosphines by oxidation-reduction condensation

A new method for the preparation of alkyl aryl sulfides from alcohols via alkoxydiphenylphosphines by oxidation-reduction condensation was established. Various primary, secondary, and tertiary alcohols were successfully converted into the corresponding su

Highly enantioselective reactions of configurationally labile α-thioorganolithiums using chiral bis(oxazoline)s via two different enantiodetermining steps

A cumene solution of α-stannyl benzyl phenyl sulfide was treated with n-BuLi and bis(oxazoline)-(l)Pr at -78 °C and subsequently with benzophenone to give the product with 99% ee. We confirmed that the reaction of α-lithio benzyl phenyl sulfide proceeds t