849590-39-2

Upstream product

• 146374-27-8 S-tert-butylsulfinimide 
• 123-11-5 4-methoxy-benzaldehyde 

Downstream Products

• 97974-64-6 1-(4-methoxyphenyl)but-3-en-1-amine 
• 35512-31-3 4⁽⁵⁾-(4-methoxyphenyl)-1H-imidazole 
• 153227-31-7 (Z)-1-bromo-4-(4-methoxystyryl)benzene 
• 1657-53-0 cis-4-methoxystilbene 

Relevant academic research and scientific papers

Carbon–Sulfur Bond Formation: Tandem Process for the Synthesis of Functionalized Isothiazoles

In this paper, we report a new process for the construction of 3,4,5-substituted isothiazoles via reaction cascades including Pummerer-like rearrangement, nucleophilic condensation, and sulfenamide cyclization followed by concomitant elimination and dehydration under mild reaction conditions. This process provides isothiazoles bearing fluorine and other functional groups in good to excellent yields from readily available starting materials.

Synthesis of Highly Functionalized Pyridines: A Metal-Free Cascade Process

Herein, we report a new process for the synthesis of highly functionalized pyridines based on a tandem Pummerer-type rearrangement, aza-Prins cyclization, and elimination-induced aromatization. This formal [5+1] cyclization provides pyridines in good yields with easily accessible starting materials. The synthetic potential of our new method is further demonstrated in the modification of the frameworks of BINOL and some natural products.

Z-Stereoselective Aza-Peterson Olefinations with Bis(trimethylsilane) Reagents and Sulfinyl Imines

Highly stereoselective aza-Peterson olefinations from bench-stable α,α-bis(trimethylsilyl)toluene reagents and N-substituted imines have been achieved using TMSO-/Bu4N+ as Lewis base activator in THF. Remarkably, and for the first time, N-t-butanesulfinyl imines were utilized for the synthesis of Z-stilbenes with excellent selectivities, while N-aryl imines generated E-stilbenes under identical reaction conditions. The protocol proved general for numerous examples with low molecular weight byproducts formed. The origin of the Z-selectivity is proposed to be a result of diastereoselective addition to N-t-butanesulfinyl imines followed by syn-elimination of an in situ formed hypervalent silicate.

Rhodium-Catalyzed Regiodivergent Hydrothiolation of Allyl Amines and Imines

The regiodivergent Rh-catalyzed hydrothiolation of allyl amines and imines is presented. Bidentate phosphine ligands with larger natural bite angles (βn ≥ 99°), for example, DPEphos, dpph, or L1, promote a Markovnikov-selective hydrothiolation in up to 88% yield and >20:1 regioselectivity. Conversely, when smaller bite angle ligands (βn ≤ 86°), for example, dppbz or dppp, are employed, the anti-Markovnikov product is formed in up to 74% yield and >20:1 regioselectivity. Initial mechanistic investigations are performed and are consistent with an oxidative addition/olefin insertion/reductive elimination mechanism for each regioisomeric pathway. We hypothesize that the change in regioselectivity is an effect of diverging coordination spheres to favor either Rh-S or Rh-H insertion to form the branched or linear isomer, respectively.

Anti-Markovnikov Hydroamination of Homoallylic Amines

The development of an anti-Markovnikov-selective hydroamination of unactivated alkenes is a significant challenge in organometallic chemistry. Herein, we present the rhodium-catalyzed anti-Markovnikov-selective hydroamination of homoallylic amines. The proximal Lewis basic amine serves to promote reactivity and enforce regioselectivity through the formation of the favored metallacycle, thus over-riding the inherent reactivity of the alkene. The scope of both the amine nucleophiles and homoallylic amines that participate in the reaction is demonstrated.

A general aminocatalytic method for the synthesis of aldimines

A general and efficient biomimetic method for the synthesis of aldimines from aldehydes and compounds bearing the NH2 group in the presence of pyrrolidine as a catalyst has been developed. These organocatalytic reactions, based on the application of the concept of nucleophilic catalysis, proceed with outstanding yields in the absence of acids and metals under simple conditions and minimum experimental manipulation. The method has been mainly applied to the synthesis of N-sulfinyl and N-sulfonyl imines, but its general validity has been proven with the preparation of representative N-phosphinoyl, N-alkyl, and N-aryl imines. These unprecedented reactions, which presumably occur via iminium activation without requiring acidic conditions, are an interesting and competitive alternative to the classical methods for preparing aldimines.

Efficient microwave-assisted synthesis of n -(tert -butylsulfinyl)imines catalyzed by amberlist-15

A general and efficient methodology is reported for the synthesis of N-(tert-butylsulfinyl)imines by using the heterogeneous catalyst amberlist-15, under microwave irradiation. Amberlist-15 is easy to handle, safe to use and quickly separable from the reaction mixture. This method offers a number of advantages including operational simplicity, inexpensive catalyst, high yield of products, and broad substrate scope.Georg Thieme Verlag Stuttgart New York.