61671-42-9

Upstream product

• 613245-36-6 1-(p-fluorophenylsulfinyl)-1-(p-fluorophenylthio)cyclohexane 
• 108-94-1 cyclohexanone 
• 110-82-7 cyclohexane 
• 2266-41-3 4-fluorobenzenesulfonylhydrazide 
• 455-15-2 4-fluorobenzenesulfinic acid methyl ester 
• 369-51-7 4-fluorobenzenesulfinic acid 
• 98-89-5 Cyclohexanecarboxylic acid 
• 371-42-6 4-Fluorothiophenol 
• 126812-30-4 1,3-dioxoisoindolin-2-yl cyclohexanecarboxylate 
• 108-85-0 1-bromocyclohexane 
• 1569-69-3 Cyclohexanethiol 
• 132993-23-8 4-fluorophenyl trifluoromethanesulfonate 
• 352-33-0 1-Chloro-4-fluorobenzene 
• 460-00-4 1-Bromo-4-fluorobenzene 

Relevant academic research and scientific papers

Visible-Light-Mediated Alkylation of Thiophenols via Electron Donor-Acceptor Complexes Formed between Two Reactants

A metal-free, photocatalyst-free, photochemical system was developed for the direct alkylation of thiophenols via electron donor-acceptor (EDA) complexes (KEDA = 145 M-1) between two reactants, N-hydroxyphthalimide esters as acceptors and thiophenol anions as donors, in the presence of a tertiary amine. The EDA complexes in the reaction system have a broad range of visible-light absorption (400-650 nm) and can trigger the reaction effectively under sunlight.

Synthesis method of alkyl sulfide compound

The invention belongs to the technical field of synthesis of organic compounds, and provides a novel method for preparing an alkyl sulfide compound. According to the method, direct synthesis preparation of the thioether compound is realized by utilizing direct coupling of an organic sulfinic acid compound and alkane under acid and illumination conditions. According to the present invention, the alkane C-H bond direct thioetherification method is adopted, the reaction functional group does not need to be configured in advance, the thioether compound synthesis reaction steps are substantially shortened, the raw materials are cheap and easily available, the conditions are mild and green, the operation is simple, convenient and safe, and the good economic prospect is provided.

Structure-Based Discovery of M-89 as a Highly Potent Inhibitor of the Menin-Mixed Lineage Leukemia (Menin-MLL) Protein-Protein Interaction

Inhibition of the menin-mixed lineage leukemia (MLL) protein-protein interaction is a promising new therapeutic strategy for the treatment of acute leukemia carrying MLL fusion (MLL leukemia). We describe herein our structure-based design, synthesis, and evaluation of a new class of small-molecule inhibitors of the menin-MLL interaction (hereafter called menin inhibitors). Our efforts have resulted in the discovery of highly potent menin inhibitors, as exemplified by compound 42 (M-89). M-89 binds to menin with a Kd value of 1.4 nM and effectively engages cellular menin protein at low nanomolar concentrations. M-89 inhibits cell growth in the MV4;11 and MOLM-13 leukemia cell lines carrying MLL fusion with IC50 values of 25 and 55 nM, respectively, and demonstrates >100-fold selectivity over the HL-60 leukemia cell line lacking MLL fusion. The determination of a co-crystal structure of M-89 in a complex with menin provides the structural basis for their high-affinity interaction. Further optimization of M-89 may lead to a new class of therapy for the treatment of MLL leukemia.

CATALYTIC C-X-BOND METATHESIS THROUGH ARYLATION

The present invention refers to a process for a catalytic aryl transfer to rearrange the backbone of aromatic C-X bonds.

Synthesis of Thioethers and Thioesters with Alkyl Arylsulfinates as the Sulfenylation Agent under Metal-Free Conditions

A study on the coupling of cycloalkanes with alkyl arylsulfinates has been performed. Using iodine as the catalyst, through C (Formula presented.) ?H bond activation and sulfinates reduction, a wide range of thioethers were produced in moderate to high yields. Additionally, various thiocarboxylic esters can also be produced by simply performing the reaction under CO pressure. Notably, this is the first report in which alkyl arylsulfinates were used as sulfenylation agents in a cross-coupling transformation.

A well-defined (POCOP)Rh catalyst for the coupling of aryl halides with thiols

This article describes a well-defined pincer-Rh catalyst for C-S cross-coupling reactions. (POCOP)Rh(H)(Cl) serves as an active precatalyst for the coupling of aryl chlorides and bromides with aryl and alkyl thiols under reasonable conditions (3% mol cat., 110 °C, 2-24 h, >90% yield). For select substrates, >90% yields were obtained with catalyst loading as low as 0.1%. Key mechanistic intermediates have been isolated and fully characterized, including (POCOP)Rh(Ph)(SPh) (6a) and (POCOP)Rh(SPh2) (6b). The aryl/bis(phosphinite) (POCOP)Rh system has been shown to favor aryl thiolate reductive elimination at elevated temperatures and in some cases at room temperature, compared with the analogous diarylamido/bis(phosphine) (PNP)Rh pincer system. Concerted reductive elimination has been studied with 6a directly and in the presence of aryl bromide and aryl chloride traps. This investigation demonstrates a clear rate dependence on aryl chloride concentration during catalysis, a dependence that is absent when using aryl bromides. The rate of catalysis is dramatically reduced or brought to zero for ortho-tolyl halides, which can be traced to slower C-S coupling and slower carbon-halogen oxidative addition for ortho-substituted aryls. The influence of the sterics in the thiol component is less straightforward. The S-H oxidative addition product (POCOP)Rh(H)(SPh) (16) has been fully characterized and its reactivity has been examined, resulting in the isolation of the sodium-thiolate adduct (POCOP)Rh(NaSPh) (19). The solid-state structure of 19 shows Na interactions not only with sulfur, but also with a neighboring Rh and the chelating aryl carbon of the pincer framework. The reactivity of 16 and 19 indicates that these potential side products should not hinder catalysis.

Metal-free preparation of cycloalkyl aryl sulfides via di-tert-butyl peroxide-promoted oxidative C(sp3)-H bond thiolation of cycloalkanes

A concise thiolation of the C(sp3)-H bond of cycloalkanes with diaryl disulfides in the presence of the oxidant di-tert-butyl peroxide (DTBP) has been developed. This reaction, without using any metal catalyst, tolerates varieties of disulfides and cycloalkanes substrates, giving good to excellent chemical yields, and thus provides a useful approach to cycloalkyl aryl sulfides from unactivated cycloalkanes.

Palladium-catalyzed thiolation of alkanes and ethers with arylsulfonyl hydrazides

A new method for the preparation of alkyl aryl sulfides through direct oxidative thiolation of alkanes or ethers with arylsulfonyl hydrazides using di-tert-butyl peroxide (DTBP) as an oxidant catalyzed by Pd(OAc)2 has been reported. The C-H bonds in various alkanes or ethers were successfully converted into C-S bonds to yield the corresponding sulfides in moderate to good yields. the Partner Organisations 2014.

Synthesis of aryl thioethers through the N -chlorosuccinimide-promoted cross-coupling reaction of thiols with Grignard reagents

A convenient one-pot approach for the synthesis of aryl sulfides through the coupling of thiols with Grignard reagents in the presence of N-chlorosuccinimide is described. The sulfenylchlorides were formed when thiols were treated with N-chlorosuccinimide, and the resulting sulfenylchlorides were then directly reacted with Grignard reagents to provide aryl sulfides in good to excellent yields under mild reaction conditions. Functional groups including ester, fluoro, and chloro are tolerated by the reaction conditions employed. It is important to note that this method has a short reaction time (30 min in total) and represents an alternative approach for the synthesis of aryl sulfides over the existing protocols.

The first example of alpha-thiomagnesiums generated from dithioacetal monoxides with Grignard reagent; their properties and some synthetic applications.

Dithioacetal monoxides were synthesized from aldehydes and cyclohexanone, and reaction of the dithioacetal monoxides with Grignard reagents was investigated. The dithioacetal monoxide synthesized from alkylaldehyde and 4-chlorobenzenethiol reacted with i-