62291-62-7

Upstream product

• 6921-34-2 benzylmagnesium chloride 
• 42881-80-1 N,N-dimethyl-4-(phenylthio)aniline 
• 100-53-8 phenylmethanethiol 
• 586-77-6 4-bromo-N,N-dimethylaniline 
• 16601-01-7 benzenethiosulfonic acid S-benzyl ester 
• 7152-80-9 4-(dimethylamino)benzenethiocyanate 
• 100-51-6 benzyl alcohol 

Downstream Products

• 42881-80-1 N,N-dimethyl-4-(phenylthio)aniline 

Relevant academic research and scientific papers

Synthesis of benzyl sulfidesviasubstitution reaction at the sulfur of phosphinic acid thioesters

An ambident electrophilicity of phosphinic acid thioesters is disclosed. Unexpected carbon-sulfur bond formation took place in the reaction between phosphinic acid thioesters and benzyl Grignard reagents. The developed method for benzyl sulfides has a wide substrate scope and was applicable for the synthesis of a drug analog.

Carbon-sulfur coupling reactions catalyzed by Pd-NHC complex

The cross-coupling reaction of aryl halides with aliphatic or aromatic thiols catalyzed by (SIPr)Pd(Py)Clis reported. This Pd-N-heterocyclic carbene (NHC) complex shows good to excellent activities toward various deactivated electron-rich aryl halides and even with unactivated aryl chlorides in C-S coupling reactions. The reactions proceeded in good yields, broad scope, and high tolerance of functional groups. The Pd-NHC complex is stable and easily to synthesize, so it is an excellent candidate to replace Pd-organophosphanes commonly used in C-S coupling catalysis. Georg Thieme Verlag Stuttgart - New York.

Preparation of polyfunctional arylmagnesium, arylzinc, and benzylic zinc reagents by using magnesium in the presence of LiCl

The presence of LiCl considerably facilitates the insertion of magnesium into various aromatic and heterocyclic bromides. Several functional groups, such as -OBoc, -OTs, -Cl, -F, -CF3, -OMe, -NMe2, and -N 2NR2, are well tolerated. The presence of a cyano group leads in some cases to competitive reduction of the organic halide to the corresponding ArH compound. The presence of sensitive groups such as methyl or ethyl ester is tolerated upon in situ trapping of the intermediate magnesium reagent with ZnCl2. This method can also be applied to the preparation of functionalized benzylic zinc reagents from benzylic chlorides. In the case of di- or tribromoaryl derivatives, directing groups such as -OPiv, -OTs, -N2NR2, or -OAc orient the zinc insertion (Zn/LiCl) to the ortho-position, while the reaction with Mg/LiCl or Mg/LiCl/ZnCl 2 leads to regioselective insertion into the para-carbon-bromine bond. Large-scale experiments (20-100 mmol) for all of the metalation procedures are described.