63877-95-2

Upstream product

• 1003-09-4 2-bromothiophene 
• 35424-56-7 1-chloro-4-(iodomethyl)benzene 
• 17151-48-3 tributyl(4-chlorophenyl)stannane 
• 873-77-8 (4-chlorphenyl)magnesium bromide 
• 188290-36-0 thiophene 
• 56636-79-4 1-tert-butoxymethyl-4-chlorobenzene 
• 636-72-6 2-thiophenemethanol 
• 122-01-0 4-chloro-benzoyl chloride 
• 63877-96-3 2-(4-fluorophenylmethyl)thiophene 
• 873-76-7 para-Chlorobenzyl alcohol 
• 104-83-6 1-Chloro-4-(chloromethyl)benzene 
• 5713-61-1 thiophen-2-yl magnesium bromide 
• 104-88-1 4-chlorobenzaldehyde 
• 3437-95-4 2-Iodothiophene 

Downstream Products

• 101336-12-3 5-(4-chlorobenzyl)thiophene-2-carbaldehyde 
• 1386262-58-3 (E)-5'-(bromo(4-chlorophenyl)methylene)-1-ethyl-4,5,6-trimethoxy-5'H-spiro[indoline-3,2-thiophen]-2-one 
• 1386262-57-2 (Z)-5'-(bromo(4-chlorophenyl)methylene)-1-ethyl-4,5,6-trimethoxy-5'H-spiro[indoline-3,2-thiophen]-2-one 
• 1386262-44-7 C₂₃H₂₁Cl₂NO₄S 
• 1386262-43-6 C₂₃H₂₁Cl₂NO₄S 

Relevant academic research and scientific papers

Cobalt-Catalyzed Formation of Functionalized Diarylmethanes from Benzylmesylates and Aryl Halides

A simple cobalt-catalyzed reductive coupling protocol allowing the synthesis of functionalized diarylmethanes from benzyl mesylate is described. The possibility to directly use the benzyl alcohol as a result of a two-step reaction is also presented. This method tolerates a variety of functional groups. A benzyl radical is likely involved. (Figure presented.).

Multimetallic Ir-Sn3-catalyzed substitution reaction of π-activated alcohols with carbon and heteroatom nucleophiles

An atom economic and catalytic substitution reaction of π-activated alcohols by a multimetallic IreSn3 complex has been demonstrated. The multimetallic IreSn3 complex can be easily synthesized from the reaction between [Cp*IrCl2]2 and SnCl2. In presence of as little as 1 mol % of the catalyst three different types of π-activated alcohols, namely benzyl, allyl, and propargyl alcohols, have been successfully transformed into alkylated products using carbon (arenes, heteroarenes, allyltrimethylsilane, and 1,3-dicarbonyls), nitrogen (sulfonamides), oxygen (alcohols), and sulfur (thiols) nucleophiles in very high yields. An electrophilic mechanism is proposed from the Hammett correlation study.

Ligand-controlled iron-catalyzed cross coupling of benzylic chlorides with aryl Grignard reagents

The selective cross coupling of benzylic chlorides with aryl Grignard reagents has been achieved by using catalytic amounts of FeCl2 and electronically tuned ortho-phenylenebisphosphine ligands. Although electron-deficient ligands promoted the reductive homocoupling of benzylic halides, electron-rich ligands effectively promoted the desired cross-coupling reaction to afford the corresponding diarylmethanes in good to excellent yields.

Synthesis of diarylmethanes via a Friedel-Crafts benzylation using arenes and benzyl alcohols in the presence of triphenylphosphine ditriflate

Triphenylphosphine ditriflate (TPPD) was found to be an efficient promoter for the Friedel-Crafts benzylation of arenes with benzyl alcohols in CH 2Cl2 at room temperature. The good yields, the 1:1 molar ratio of arene and benzyl alcohol, the benzylation of chlorobenzene as a nonactivated aromatic compound at room temperature, and no by-product formation are the main advantages of this procedure.

Friedel-crafts benzylation of activated and deactivated arenes

NO going back makes possible facile Friedel-Crafts benzylations with moderate reaction temperatures, simple reaction workups, and improved substrate scope for the formation of synthetically important diarylmethanes (see scheme). Upon complexation with BF3?OEt2, hydroxamates serve as reversible leaving groups that stabilize highly reactive carbocations. Even deactivated arenes and electron-deficient benzylhydroxamates react cleanly under these conditions.

Efficient and selective alkylation of arenes and heteroarenes with benzyl and allyl ethers using a Ir/Sn bimetallic catalyst

A high-valent heterobimetallic catalyst namely [Ir2(COD)2(SnCl3)2(Cl)2(μ-Cl)2] (5 mol %), or dual catalyst system of [Ir(COD)Cl]2 (1 mol %) and SnCl4 (4 mol %), promotes the benzylation or allylation of arenes and heteroarenes using ethers as the alkylating agents. An electrophilic mechanism is proposed from a Hammett correlation.

Efficient Pd-catalyzed heterobenzylic cross-coupling using sulfonium salts as substrates and (PhO)3P as a supporting ligand

S-(2-Furanylmethyl)tetramethylenesulfonium hexafluorophosphate, S-(2-thienylmethyl)tetramethylenesulfonium hexafluorophosphate, S-(3-thienylmethyl)tetramethylenesulfonium hexafluorophosphate, and S-(N-tert-butoxycarbonyl-2-pyrrolylmethyl)tetramethylenesulfonium hexafluorophosphate have been conveniently prepared from the corresponding alcohols. These stable heterobenzylic sulfonium salts participate in palladium-catalyzed Stille cross-couplings with organostannanes. All but the last mentioned sulfonium salt are also active participants in palladium-catalyzed cross-coupling reactions with boronic acids and organozinc halides. Because the heterobenzylic cross-coupling reactants are potent alkylating agents, they scavenge the typical phosphines and arsines that otherwise could be used to stabilize the palladium catalyst over extended reaction times. This problem was overcome by the use of (PhO)3P as a unique supporting ligand for the palladium-catalyzed cross-coupling of heterobenzylic sulfonium salts.

Process for the preparation of methylene compounds and the novel compound 2-(2,4-Dichloro-5-fluorobenzyl)thiophene

Methylene compounds are preferably prepared by reducing an aluminum halide complex of the formula STR1 in which R1 represents a C6 -C10 -aryl radical which is optionally substituted by 1 to 4 C1 -C4 -alkyl radicals, 1 to 4 fluorine, chlorine and/or bromine atoms, one C1 -C8 -alkoxy group and/or one acetoxy group, or represents a heteroaryl radical which is optionally substituted by one C1 -C4 -alkyl radical and/or one fluorine, chlorine or bromine atom and contains 5 to 10 C atoms and one O or S atom and R2 represents a C1 -C12 -alkyl radical which is optionally substituted by 1 to 5 fluorine, chlorine and/or bromine atoms, independently of R1 represents a radical as defined for R1 and, in the case where R1 =a C6 -C10 -aryl radical which is substituted by 1 to 4 fluorine, chlorine and/or bromine atoms, also represents a furyl or thienyl radical, Y represents fluorine, chlorine or bromine, with an amineborane of the formula STR2 in which R3 represents C1 -C4 -alkyl and R4 represents hydrogen or C1 -C4 -alkyl and/or with sodium borohydride and/or with potassium borohydride. 2-(2,4-Dichloro-5-fluorobenzyl)thiophene is obtainable in this way for the first time.

A general, convenient and highly efficient synthesis of diarylmethanes by copper-catalyzed reaction

Copper-catalyzed reactions of arylmagnesium derivatives with benzyliodides have been developed for the large scale preparation of diarylmethanes. Various diarylmethanes have been prepared in high yield by this reaction, the amount of homocoupled dimers be

BASE CLEAVAGE OF SUBSTITUTED - AND -TRIMETHYLSILANE. STABILIZATION OF CARBANIONIC CENTRES BY 2-THIENYL AND 2-FURYL GROUPS

Rates of cleavage by NaOMe-MeOH at 25 deg C have been determined for (2-thienyl)2CHSiMe3 and for the compounds Ph(2-thienyl)CHSiMe3 and Ph(2-furyl)CHSiMe3 and some of their derivatives with a substituent in the m- or p-position of the phenyl group or the