155061-60-2

Upstream product

• 578-57-4 2-bromoanisole 
• 51934-41-9 4-iodobenzoic acid ethyl ester 
• 529-28-2 4-iodoanisol 
• 5798-75-4 Ethyl 4-bromobenzoate 
• 64-17-5 ethanol 
• 5720-06-9 2-Methoxyphenylboronic acid 
• 86487-17-4 2-tri-n-butylstannylanisole 
• 348-06-1 p-carboethoxybenzenediazonium tetrafluoroborate 
• 94-09-7 p-aminoethylbenzoate 

Downstream Products

• 5728-32-5 4-(2-methoxyphenyl)benzoic acid 

Relevant academic research and scientific papers

Gold(i)-catalyzed cross-coupling reactions of aryldiazonium salts with organostannanes

Gold(i)-catalyzed cross-coupling reactions of aryldiazonium salts with organostannanes are described. This redox neutral strategy offers an efficient approach to diverse biaryls, vinyl arenes and arylacetylenes. Monitoring the reaction with NMR and ESI-MS provided strong evidence for the in situ formation of Ph3PAuIR (R = aryl, vinyl and alkynyl) species which is crucial for the activation of aryldiazonium salts.

Stannylation of Aryl Halides, Stille Cross-Coupling, and One-Pot, Two-Step Stannylation/Stille Cross-Coupling Reactions under Solvent-Free Conditions

Solvent-free protocols for palladium-catalyzed stannylation of aryl halides, Stille cross-coupling, and one-pot, two-step stannylation/Stille cross-coupling (SSC) are reported for the first time. (Het)aryl halides bearing acceptor, donor, as well as sterically demanding substituents are stannylated and/or coupled in high yields. The reactions are catalyzed by conventional palladium(II) acetate/PCy3 [Pd(OAc)2/PCy3] under air, using available base CsF, and without the use of high purity reagents. The developed synthetic procedures are versatile, robust, and easily scalable. The absence of solvent, and the elimination of isolation procedures of aryl stannanes makes the SSC protocol simple, step economical, and highly efficient for the synthesis of biaryls in a one-pot two-step procedure.

Highly functionalized biaryls via Suzuki-Miyaura cross-coupling catalyzed by Pd@MOF under batch and continuous flow regimes

A diverse set of more than 40 highly functionalized biaryls was synthesized successfully through the Suzuki-Miyaura cross-coupling reaction catalyzed by Pd nanoparticles supported in a functionalized mesoporous MOF (8 wt% Pd@MIL-101(Cr)-NH2). This could be achieved under some of the mildest conditions reported to date and a strong control over the leaching of metallic species could be maintained, despite the presence of diverse functional groups and/or several heteroatoms. Some of the targeted molecules are important intermediates in the synthesis of pharmaceuticals and we clearly exemplify the versatility of this catalytic system, which affords better yields than currently existing commercial procedures. Most importantly, Pd@MIL-101-NH2 was packed in a micro-flow reactor, which represents the first report of metallic nanoparticles supported on MOFs employed in flow chemistry for catalytic applications. A small library of 11 isolated compounds was created in a continuous experiment without replacing the catalyst, demonstrating the potential of the catalyst for large-scale applications.

Method of manufacturing hydroxybiphenyls

PROBLEM TO BE SOLVED: To provide a convenient production method of biphenyls which become the raw materials of medicines, pesticides and functional materials. SOLUTION: In the presence of a palladium catalyst and an alkali metal carboxylate, a 2,2'-bi(1,3,2-benzodioxaborole) derivative represented by general formula (1) (in formula, R1represents a hydrogen atom or a 1-4C alkyl group) and a benzene derivative A are made to react with each other, next, in the presence of an alkali metal phosphate or an alkali metal carbonate, a benzene derivative B is made to react therewith, and biphenyls represented by general formula (4) (in formula, each of R2and R3represents a hydrogen atom, a halogen atom, or the like, and each of n and m represents an integer of 1 to 4) are produced. COPYRIGHT: (C)2013,JPOandINPIT

Generation of arylzinc reagents through an iodine-zinc exchange reaction promoted by a non-metallic organic superbase

Functionalized aryl and heteroaryl zinc reagents were prepared from aryl iodides and diethylzinc through t-Bu-P4 base-promoted iodine-zinc exchange reactions. The scope and limitations of this protocol, and several applications for the synthesis of oligoaryls and fused aromatics, are presented.

Efficient cobalt-catalyzed formation of unsymmetrical biaryl compounds and its application in the synthesis of a sartan intermediate

(Chemical Equation Presented) No prior preparation of the organometallic reagent is required in a cobalt-catalyzed coupling of two different aryl halides under mild conditions (see scheme). A broad spectrum of valuable biaryl compounds can be prepared in this way. Not only may a variety of reactive substituents be present, but heteroaryl halides and aryl triflates are also suitable substrates. DMF = N,N-dimethylformamide, FG = functional group.

Effective Pd-nanoparticle (PdNP)-catalyzed negishi coupling involving alkylzinc reagents at room temperature

(Chemical Equation Presented) Pd(OAc)2 is an efficient catalyst precursor for Negishi coupling in the presence of Bu4NBr. Secondary and primary alkylzinc reagents with β-H and arylzinc reagents all reacted with aryl iodides at temper

Use of functionalized onium salts as a soluble support for organic synthesis

The invention relates to the use of a onium salt functionalized by at least one organic function, as a soluble support, in the presence of at least one organic solvent, for organic synthesis of a molecule, in a homogenous phase, by at least one transformation of said organic function. The onium salt enables the synthesized molecule to be released. The onium salt is present in liquid or solid form at room temperature and corresponds to formula A1+, X1?, wherein A1+ represents a cation and X1? represents an anion.

Biphenyl vasopressin agonists

A compound of the formulae (I) or (II): wherein: Y is a moiety selected from NR or —(CH2)n; wherein R is hydrogen or (C1-C6) lower alkyl, and n is 1; represents: (1) a phenyl ring optionally substituted with one

Synthesis of unsymmetrical biaryls by electroreductive cobalt-catalyzed cross-coupling of aryl halides

The consumable anode process allows the electrochemical cross-coupling reaction between various functionalized aromatic halides (iodides, bromides and chlorides) in the presence of cobalt halides as catalyst in a mixed solvent acetonitrile/pyridine (9:1). A great variety of unsymmetrical biaryls are obtained in moderate to excellent yields.