58666-77-6

Upstream product

• 110-00-9 furan 
• 623-00-7 4-bromobenzenecarbonitrile 
• 3058-39-7 4-iodobenzonitrile 
• 661-69-8 hexamethyldistannane 
• 16643-09-7 trimethylstannylsodium 
• 186886-56-6 (4-cyanophenyl)trimethylammonium methylsulfate 
• 873-74-5 4-Aminobenzonitrile 
• 21382-98-9 p-cyanophenyl methyl sulfide 
• 36801-01-1 4-cyanobenzenethiol 
• 77976-02-4 4-cyanobenzoyl fluoride 
• 6068-72-0 4-cyanobenzoyl chlorIde 
• 623-03-0 4-Cyanochlorobenzene 
• 1066-45-1 trimethyltin(IV)chloride 
• 7440-23-5 sodium 

Downstream Products

• 1503-49-7 p-cyanobenzophenone 
• 2920-38-9 4-cyano-1,1'-biphenyl 
• 57774-36-4 4-(4'-chlorophenyl)benzonitrile 
• 194939-76-9 2-naphthyl 4-cyanophenyl ketone 
• 19812-93-2 4-Cyano-4'-hydroxybiphenyl 

Relevant academic research and scientific papers

Synthesis of Arylstannanes via Palladium-Catalyzed Decarbonylative Coupling of Aroyl Fluorides

Aryl stannanes are valuable precursors in organic transformations, but their synthetic methods are limited. Here we present a Pd-catalyzed decarbonylative stannylation of acid fluorides in the absence of exogenous base. Various aryl stannanes were efficiently prepared from bench-stable transition metal catalyst and ligand with broad functional group compatibility and substrate scope including natural products and pharmaceuticals. This protocol was also successfully used to a late-stage diversification of an existing uricosuric drug probenecid. (Figure presented.).

Transition-Metal-Free Aryl-Heteroatom Bond Formation via C-S Bond Cleavage

Aryl-heteroatom bonds (C-Het) are almost ubiquitously present in chemical molecules. However, methods for diverse C-Het bond formations from a simple substrate are limited. Herein, we report a convenient and efficient C-S bond transformation of aryl sulfoniums to various C-Het bonds (C-O, C-S, C-Sn, C-Si, C-Se) in the absence of any transition-metal catalyst. These reactions proceeded in mild conditions with a wide substrate scope.

Visible-Light-Driven Synthesis of Arylstannanes from Arylazo Sulfones

The visible-light-driven preparation of (hetero)aryl stannanes was carried out under both photocatalyst- and metal-free conditions via irradiation of arylazo sulfones in the presence of hexaalkyldistannanes. The reaction shows a high efficiency and a wide substrates scope. The resulting crude organotin derivatives can be directly employed in a Stille protocol.

Synthesis of Aryl Trimethylstannane via BF3·OEt2-Mediated Cross-Coupling of Hexaalkyl Distannane Reagent with Aryl Triazene at Room Temperature

BF3·OEt2-mediated cross-coupling of (SnMe3)2 with aryl triazene offers a new strategy for the synthesis of aryl stannane. A variety of synthetically useful aryl trimethylstannanes were produced in moderate to good yields with this metal-free approach. One-pot sequential Stille cross-coupling with different aryl bromides provides a short entry to both symmetrical and unsymmetrical biaryl compounds.

Synthesis of aryl trimethylstannanes from aryl halides: An efficient photochemical method

An efficient transition-metal-free photochemical method featuring excellent functional group tolerance, mild reaction conditions and short reaction times has been discovered and developed for the synthesis of (hetero)aryl trimethylstannanes from (hetero)aryl halides. A photo-initiated radical chain mechanism was proposed based on preliminary mechanistic studies.

1,2-AZABORINE COMPOUNDS AND SYNTHESIS

A compound, or a pharmaceutically acceptable salt or ester thereof, having a structure of formula (I), wherein R1 is a substituted aryl or an optionally-substituted heteroaryl, provided that the heteroaryl is not pyridyl or azaborine; and each

Indium-mediated regioselective synthesis of ketones from arylstannanes under solvent-free ultrasound irradiation

The solvent-free indium-promoted reaction of alkanoyl chlorides with sterically and electronically diverse arylstannanes is a simple and direct method for the regioselective synthesis of primary, secondary and tertiary alkyl aryl ketones in good to excellent isolated yields (42-84%) under mild and neutral conditions. The protocol is also adequate for the synthesis of aryl vinyl ketones. Reaction times are drastically reduced (from 3-32 h to 10-70 min) under ultrasonic irradiation. Evidences for the involvement of a homolytic aromatic ipso-substitution mechanism, in which indium metal acts as radical initiator, are presented. It is possible the transference of two aryl groups from tin, thus improving effective mass yield, working with diarylstannanes as starting substrates.

Synthesis of aryl trimethylstannanes from aryl amines: A sandmeyer-type stannylation reaction

Sandmeyer-type stannylation: Stille coupling is one of the most powerful coupling reactions for C-C bond formation, whereas there are only limited methods to access aryl stannane compounds. A mild stannylation process based on a Sandmeyer-type transformation using aromatic amines as the starting materials is described. DCE: 1,2-dichloroethane. Copyright

Rhodium-catalyzed boron arylation of 1,2-azaborines

A Sn-phony in B! BN isosteres of biphenyl compounds are prepared through Rh-catalyzed cross-coupling between 2-chloro-1,2-azaborines and arylstannanes (see scheme). The synthetic method should enable investigations of structure-activity relationships (SAR

Synthesis of arylstannanes from arylamines

Arylamines have been converted into aryltrimethylammonium salts, which on reaction with sodium trimethylstannide (1) in liquid ammonia afford aryltrimethylstannanes by the SRN1 mechanism. With (4-methoxyphenyl)- (2), (1-naphthyl)- (4), phenyl- (6), (4-acetylphenyl)- (8), and (4-cyanophenyl)trimethylammonium salts (10) the substitution products are obtained in good to excellent yields (45-100%). Also, the photo-stimulated reaction of (2-pyridyl)trimethylammonium iodide (12) with 1 leads to the substitution product 13 (50%). With (4-chlorophenyl)trimethylammonium iodide (14) the disubstitution product 19 is obtained in 76% yield. On the other hand, the results obtained in the reaction of (4-bromophenyl)trimethylammonium iodide (15) with 1 clearly indicate a fast HME reaction in the dark. The ET process (SRN1) competes, although inefficiently, under irradiation.