23349-16-8

Upstream product

• 1121-86-4 1-Fluoro-3-iodobenzene 
• 1066-54-2 trimethylsilylacetylene 
• 152574-69-1 1-(3-fluorobenzyl)benzotriazole 
• 75-20-7 calcium carbide 
• 471-25-0 Propiolic acid 
• 2561-17-3 1-ethynyl-3-fluoro-benzene 
• 1073-06-9 3-fluorobromobenzene 
• 58606-65-8 N-[(3-fluorophenyl)methylidene]aniline 
• 23349-13-5 1,1-Di-(m-fluorphenyl)-2-bromethylen 
• 164362-60-1 (3-fluorophenyl)methylenebenzenamine 

Downstream Products

• 1404432-66-1 2,3-bis(3-fluorophenyl)-1-(iodomethyl)-1-methyl-1H-indene 
• 1584632-96-1 5,6-bis(3-fluorophenyl)-2H-pyran-2-one 
• 1268467-94-2 methyl (E)-2,3-bis(3-fluorophenyl)acrylate 
• 1268468-01-4 (E)-2,3-bis(3-fluorophenyl)prop-2-en-1-ol 

Relevant academic research and scientific papers

Ruthenium(ii)-catalyzed intermolecular annulation of alkenyl sulfonamides with alkynes: Access to bicyclic sultams

A ruthenium-catalyzed allylic C(sp3)-H activation strategy has been employed to develop an intermolecular coupling of alkenyl sulfonamides with alkynes. This protocol features the diastereoselective construction of [3.3.0] and [4.3.0] bicyclic sultams in one step.

Asymmetric Dearomatization of Indole by Palladium/PC-Phos-Catalyzed Dynamic Kinetic Transformation

A palladium-catalyzed intermolecular dynamic kinetic asymmetric dearomatization of 3-arylindoles with internal alkynes was developed with the use of achiral Xantphos and chiral sulfinamide phosphine ligand (PC-Phos) as the co-ligands. This method could deliver various spiro[indene-1,3′-indole] compounds in good yields (up to 95 % yield) with up to 98 % ee. The salient features of the transformation include the use of readily available substrates, ease of scale-up and the versatile functionalization of the products. The mechanistic experiments gave some insights on active intermediates.

Palladium-catalyzed sequential three-component reactions to access vinylsilanes

A palladium-catalyzed sequential three-component reaction has been developed. The palladacycles, generated through cascade reactions of aryl halides and alkynes, are the key intermediates and react with hexamethyldisilane to form disilylated products. The reaction represents a useful preparative method for vinylsilanes, and the vinylsilanes can be transformed into tetrasubstituted alkenes.

Palladium-Nanoparticles-Catalyzed Oxidative Annulation of Benzamides with Alkynes for the Synthesis of Isoquinolones

A novel method to synthesize isoquinolones via oxidative annulation of N-alkoxy benzamides and alkynes using binaphthyl-stabilized palladium nanoparticles (Pd-BNP) as catalyst has been developed. This methodology affords various isoquinolone derivatives in good to excellent yields with high regioselectivities in the presence of air as oxidant. N-Methoxybenzothioamide was also found to undergo oxidative annulation with alkyne successfully and provided a sulfur analogue of isoquinolones in moderate yields. The Pd-BNP catalyst was easily recovered and reused up to four times without any apparent agglomeration. (Figure presented.).

Cooperative Lewis acid-onium salt catalysis as tool for the desymmetrization of meso-epoxides

Epoxide desymmetrizations by bromide are very rare despite the large synthetic potential of chiral bromohydrins. Herein we present a new concept for epoxide desymmetrizations in which a bifunctional Lewis acid/ammonium salt catalyst allows for efficient enantio-selective epoxide ring openings by Br. With acetylbromide as a Br source bromohydrin esters are formed.

Cobalt(III)-Catalyzed Redox-Neutral Synthesis of Unprotected Indoles Featuring an N-N Bond Cleavage

A redox-neutral cobalt(III)-catalyzed synthetic approach for the direct synthesis of unprotected indoles showcasing an N-N bond cleavage is reported. The herein newly introduced Boc-protected hydrazines establish a beneficial addition to the limited portfolio of oxidizing directing groups for cobalt(III) catalysis. Moreover, the developed catalytic methodology tolerates a good variety of functional groups.

Palladium-catalyzed oxidative annulation of acrylic acid and amide with alkynes: A practical route to synthesize α-pyrones and pyridones

A range of internal alkynes smoothly underwent palladium-catalyzed oxidative annulations with acrylic acid and amide to afford α-pyrones and pyridones in good to excellent yields with high regioselectivity. The usage of O2 (1 atm) as a stoichiometric oxidant with H2O as the only byproduct under mild conditions makes this process more attractive and practical.

A conjunctive carboiodination: Indenes by a double carbopalladation- reductive elimination domino process

Something gained, nothing lost: A Pd0-catalyzed domino intermolecular/intramolecular process terminated by carbohalogenation is reported. In this reaction, two new C-C bonds, one new C-I bond and one five-membered ring are formed in a single step, and all of the atoms in the starting materials are incorporated into the product (see scheme). Copyright

Synthesis of symmetrical diarylalkyne from palladium-catalyzed decarboxylative couplings of propiolic acid and aryl bromides under water

Symmetric diarylalkynes were obtained from the decarboxylative coupling reactions of aryl bromides and propiolic acid in water solvent condition. In the presence of phase transfer surfactant C18H37N(CH 3)3Cl, the catalytic system of both Pd(PPh 3)2Cl2/dppb and Pd(TPPMS)2Cl 2/TPPMS afforded the desired coupled products in good yields.

One-pot synthesis of symmetrical and unsymmetrical bisarylethynes by a modification of the sonogashira coupling reaction.

A modification of the Sonogoshira coupling reaction employing an amidine base and a substoichiometric amount of water generates symmetrical and unsymmetrical bisarylethynylenes in one pot through in situ deprotection of trimethylsilylethynylene-added intermediates.