46190-45-8

Upstream product

• 619-42-1 4-methoxycarbonylphenyl bromide 
• 540-51-2 2-bromoethanol 
• 75867-41-3 4-trimethylsilanylethynyl-benzoic acid methyl ester 
• 106918-31-4 1-methoxy-2-(4-carbomethoxyphenyl)ethylene 
• 1571-08-0 methyl 4-formylbenzoate 
• 36099-25-9 <4-(methoxycarbonyl)phenyl>oxirane 
• 1584730-57-3 methyl 4-[2-(phenylsilyl)ethyl]benzoate 
• 1076-96-6 methyl 4-vinylbenzoate 
• 1075-49-6 4-ethenylbenzoic acid 

Downstream Products

• 99-75-2 4-methyl-benzoic acid methyl ester 
• 7364-20-7 4-ethyl-benzoic acid methyl ester 
• 113249-86-8 Methyl 4-(2-Trimethylsiloxyethyl)benzoate 
• 136333-97-6 methyl 4-(2-bromoethyl)benzoate 
• 106918-32-5 4-carbomethoxyphenylacetaldehyde 

Relevant academic research and scientific papers

Ni-Catalyzed Formal Cross-Electrophile Coupling of Alcohols with Aryl Halides

Direct coupling of unactivated alcohols remains a challenge in current synthetic chemistry. We herein demonstrate a strategy building upon in situ halogenation/reductive coupling of alcohols with aryl halides to forge Csp2-Csp3 bonds. The combination of 2-chloro-3-ethylbenzo[d]oxazol-3-ium salt (CEBO) and TBAB as the mild bromination reagents enables rapid transformation of a wide range of alcohols to their bromide counterparts within one to 5 min in CH3CN and DMF, which is compatible with the Ni-catalyzed cross-electrophile coupling conditions in the presence of a chemical reductant. The present method is suitable for arylation of a myriad of structurally complex alcohols with no need for prepreparation of alkyl halides. More importantly, the mild and kinetically rapid bromination process has shown good selectivity in the bromination/arylation of symmetric diols and less sterically hindered hydroxyl groups in polyols, thus offering promise for selective functionalization of diols and polyols without laborious protecting/deprotecting operations. The practicality of this work is also evident in the arylation of a number of carbohydrates, drug compounds, and naturally occurring alcohols.

Chemoselective Cleavage of Si-C(sp3) Bonds in Unactivated Tetraalkylsilanes Using Iodine Tris(trifluoroacetate)

Organosilanes are synthetically useful reagents and precursors in organic chemistry. However, the typical inertness of unactivated Si-C(sp3) bonds under conventional reaction conditions has hampered the application of simple tetraalkylsilanes in organic synthesis. Herein we report the chemoselective cleavage of Si-C(sp3) bonds of unactivated tetraalkylsilanes using iodine tris(trifluoroacetate). The reaction proceeds smoothly under mild conditions (-50 °C to room temperature) and tolerates various polar functional groups, thus enabling subsequent Tamao-Fleming oxidation to provide the corresponding alcohols. NMR experiments and density functional theory calculations on the reaction indicate that the transfer of alkyl groups from Si to the I(III) center and the formation of the Si-O bond proceed concertedly to afford an alkyl-λ3-iodane and silyl trifluoroacetate. The developed method enables the use of unactivated tetraalkylsilanes as highly stable synthetic precursors.

Synthesis of remote fluoroalkylated alkenes by a palladium-catalyzed relay Heck-type reaction

Herein, we report a palladium-catalyzed relay Heck-type reaction of fluoroalkyl bromide and terminal alkenes. The reaction involves fluoroalkylation of alkenes and migration of double bonds via a 1,5-hydrogen atom transfer strategy. Through this method, a

PROTEOLYSIS TARGETING CHIMERA (PROTACS) AS DEGRADERS OF SMARCA2 AND/OR SMARCA4

The present invention encompasses compounds of formula (I) wherein the groups R1,A, G, LK and t have the meanings given in the claims and specification, their use as degraders of SMARCA2 and/or SMARCA4, pharmaceutical compositions which contain compounds of this kind and their use as medicaments/medical uses, especially as agents for treatment and/or prevention of oncological diseases.

Piers' borane-mediated hydrosilylation of epoxides and cyclic ethers

We report the first diarylborane-catalysed hydrosilylation of epoxides and cyclic ethers. Mechanistic studies on the in situ generated Piers' borane (C6F5)2BH with hydrosilanes in the presence of an epoxide revealed that an alkyloxy(diaryl)borane (C6F5)2BOR is readily formed as a catalytically competent species for the outer-sphere hydrosilylation of epoxides and cyclic ethers.

Iron-catalysed chemo-, regio-, and stereoselective hydrosilylation of alkenes and alkynes using a bench-stable iron(II) pre-catalyst

The chemo-, regio-, and stereoselective iron-catalysed hydrosilylation of alkenes and alkynes with excellent functional group tolerance is reported (34 examples, 41-96% yield). The catalyst and reagents are commercially available and easy to handle, with the active iron catalyst being generated in situ, thus providing a simple and practical methodology for iron-catalysed hydrosilylation. The silane products can be oxidised to the anti-Markovnikov product of olefin hydration, and the one-pot iron-catalysed hydrosilylation-oxidation of olefins to give silane(di)ols directly is also reported. The iron pre-catalyst was used at loadings as low as 0.07 mol%, and displayed catalyst turnover frequencies (TOF) approaching 60,000 molh-1. Initial mechanistic studies indicate an iron(I) active catalyst.

Evaluation of N-phenyl homopiperazine analogs as potential dopamine D 3 receptor selective ligands

A series of N-(2-methoxyphenyl)homopiperazine analogs was prepared and their affinities for dopamine D2, D3, and D4 receptors were measured using competitive radioligand binding assays. Several ligands exhibited high binding affinity and selectivity for the D3 dopamine receptor compared to the D2 receptor subtype. Compounds 11a, 11b, 11c, 11f, 11j and 11k had Ki values ranging from 0.7 to 3.9 nM for the D3 receptor with 30- to 170-fold selectivity for the D 3 versus D2 receptor. Calculated log P values (log P = 2.6-3.6) are within the desired range for passive transport across the blood-brain barrier. When the binding and the intrinsic efficacy of these phenylhomopiperazines was compared to those of previously published phenylpiperazine analogues, it was found that (a) affinity at D2 and D3 dopamine receptors generally decreased, (b) the D3 receptor binding selectivity (D2:D3 Ki value ratio) decreased and, (c) the intrinsic efficacy, measured using a forskolin-dependent adenylyl cyclase inhibition assay, generally increased.

Enantioselective hydrosilylation of aromatic alkenes catalyzed by chiral bis(oxazolinyl)phenyl-rhodium acetate complexes

Highly efficient and enantioselective hydrosilylation of aromatic alkenes catalyzed by the chiral rhodium acetate complexes with the bis(oxazolinyl)phenyl ligands has been reported that afforded chiral silane derivatives with up to 99% ee. Georg Thieme Ve

Building addressable libraries: The use of a mass spectrometry cleavable linker for monitoring reactions on a microelectrode array

Time-of-flight secondary ion mass spectrometry (TOF SIMS) has been used in conjunction with a mass spectrometry cleavable linker to determine the percent conversion of reactions that were conducted site-selectively on an addressable microelectrode array.

Synthesis and in vitro binding of N-phenyl piperazine analogs as potential dopamine D3 receptor ligands

The synthesis of a series of N-(2-methoxyphenyl)piperazine and N-(2,3-dichlorophenyl)piperazine analogs and their in vitro binding affinities for dopamine D2, D3, D4 are presented. A series of N-(2-methoxyphenyl)piperazine