51246-20-9

Upstream product

• 98-81-7 1-bromovinylbenzene 
• 1021-45-0 phosphoric acid diethyl ester-(1-phenyl-vinyl ester) 
• 16029-98-4 trimethylsilyl iodide 
• 536-74-3 phenylacetylene 
• 28143-79-5 1-phenyl vinyl triflate 
• 98-86-2 acetophenone 
• 100-42-5 styrene 
• 2170-06-1 1-Phenyl-2-(trimethylsilyl)acetylene 
• 13466-30-3 (1-phenylethylidene)hydrazine 

Downstream Products

• 89523-71-7 2-phenyl-1-undecen-3-ol 
• 2699-87-8 1,2-diphenyl-2-propen-1-ol 
• 22744-94-1 N,N-diethyl-2-phenyl-acrylamide 
• 81245-63-8 3,4-diphenyl-1,2,4-pentatriene 
• 869307-95-9 2-[dimethyl-(2-phenyl-allyl)-silanyl]-pyridine 
• 64859-23-0 α-phenylacrylanilide 
• 19199-47-4 2-phenyl-1-(piperidin-1-yl)prop-2-en-1-one 
• 19199-46-3 1-morpholino-2-phenylprop-2-en-1-one 
• 77670-30-5 diethyl 2-(3-oxo-1,3-diphenylpropyl)malonate 
• 634603-25-1 2-(1-methyl-3-oxo-3-phenyl-propyl)-malonic acid diethyl ester 
• 1062573-03-8 diethyl N-(1-phenyl-ethen-1-yl-carbonyl)-α-aminobenzyl-phosphonate 
• 1133035-26-3 4-methyl-1-(1-phenylvinyl)-4-vinylazetidin-2-one 

Relevant academic research and scientific papers

Amino- and azidocarbonylation of iodoalkenes

Iodoalkenes, available from ketones via their hydrazones, underwent palladium-catalysed azidocarbonylation. Depending on the structure of the acyl azides, consecutive hydrolysis toward corresponding primary amides was observed. ‘Direct’ aminocarbonylation

Synthesis of Unsymmetrical 1,4-Dicarbonyl Compounds by Photocatalytic Oxidative Radical Additions

Herein we report a photocatalytic oxidative radical addition reaction for the synthesis of unsymmetrical 1,4-dicarbonyl compounds. This reaction utilizes a desulfurization process to generate electrophilic radicals, which add to α-halogenated alkenes and undergo further oxidation to deliver 1,4-dicarbonyl compounds. This mild and highly efficient method provides a valuable alternative to known strategies.

Oxidative Addition of Alkenyl and Alkynyl Iodides to a AuI Complex

The first isolated examples of intermolecular oxidative addition of alkenyl and alkynyl iodides to AuI are reported. Using a 5,5′-difluoro-2,2′-bipyridyl ligated complex, oxidative addition of geometrically defined alkenyl iodides occurs readily, reversibly and stereospecifically to give alkenyl-AuIII complexes. Conversely, reversible alkynyl iodide oxidative addition generates bimetallic complexes containing both AuIII and AuI centers. Stoichiometric studies show that both new initiation modes can form the basis for the development of C?C bond forming cross-couplings.

Ready access to organoiodides: Practical hydroiodination and double-iodination of carbon-carbon unsaturated bonds with I2

By using I2 or I2/H3PO3 system, various alkenes and alkynes were converted to the corresponding alkyl and alkenyl iodides in good yields. In the presence of I2, alkynes could be di-iodinated using H2O as the solvent in air at room temperature. This method also features the simple work-up procedure since the pure product could be obtained by extraction. Additionally, for the first time, combining with the non-toxic and cheap phosphonic acid H3PO3, alkenes and alkynes were also hydroiodinated successfully, which provides a simple and practical approach for synthesis of organoiodides.

Metal-Free Transfer Hydroiodination of C-C Multiple Bonds

The design and a gram-scale synthesis of a bench-stable cyclohexa-1,4-diene-based surrogate of gaseous hydrogen iodide are described. By initiation with a moderately strong Br?nsted acid, hydrogen iodide is transferred from the surrogate onto C-C multiple bonds such as alkynes and allenes without the involvement of free hydrogen iodide. The surrogate fragments into toluene and ethylene, easy-to-remove volatile waste. This hydroiodination reaction avoids precarious handling of hydrogen iodide or hydroiodic acid. By this, a broad range of previously unknown or difficult-to-prepare vinyl iodides can be accessed in stereocontrolled fashion.

Copper-catalyzed tandem reaction directed toward synthesis of 2,2-disubstituted quinazolinones from vinyl halides and 2-aminobenzamides

A copper-catalyzed tandem reaction with vinyl halides and 2-aminobenzamides has been developed. In this synthetic route, cross-coupling reaction of the amide moiety with vinyl halides initially progresses, followed by hydroamination, to provide 2,2-disubstituted quinazolinone derivatives. Moreover, the tandem reaction is used in a one-pot synthesis beginning with alkyne hydroiodination by PPh3, I2, and H2O.

Catalytic Enantioselective Synthesis of Halocyclopropanes

A catalytic asymmetric synthesis of halocyclopropanes is described. The developed method is based on a carbenoid cyclopropanation of 2-haloalkenes with tert-butyl α-cyano-α-diazoacetate using a chiral rhodium catalyst that permits access to a broad range

Gold-Catalyzed Imination/Mannich Reaction Cascades of 3-En-1-ynamides with Anilines and Aldehydes to Enable 1,5-Nitrogen Functionalizations

Gold-catalyzed imination/Mannich reaction cascades on readily available 3-en-1-ynamides enable the diastereoselective synthesis of 1,5-iminoamino compounds in a one-pot operation. The reactions work well with diversified 3-en-1-ynamides, aldehydes and anilines with good to excellent diastereoselectivities. Our control experiments indicate gold-catalyzed aminations of 3-en-1-ynamides to yield α-imino allylgold intermediates that react subsequently with iminiums to implement the Mannich reactions stereoselectively. The reactions proceed with anti-selectivity for those 3-en-1-ynamides bearing acyclic alkenes whereas syn-selectivity is seen for their cycloalkene-based analogues. An open-transition state can satisfactorily rationalize these observed stereoselectivities based on an antiperiplanar conformation.

Selective Ruthenium-Catalyzed Hydrochlorination of Alkynes: One-Step Synthesis of Vinylchlorides

An unprecedented ruthenium-catalyzed direct and selective alkyne hydrochlorination is reported and leads to vinylchlorides in excellent yields with atom economy. The reaction proceeds at room temperature from terminal alkynes and provides a variety of chloroalkenes. Only the regioisomer resulting from the formal Markovnikov addition is selectively formed. Mechanistic studies show the stereoselective syn addition of HCl to alkynes at room temperature and suggest a chloro hydrido RuIV species as a key intermediate of the reaction.

A convenient hydroiodination of alkynes using I2/PPh3/H2O and its application to the one-pot synthesis of trisubstituted alkenes via iodoalkenes using Pd-catalyzed cross-coupling reactions

A facile hydroiodination of alkynes using readily-available reagents such as I2, PPh3, and H2O has been developed. This is extended to the one-pot synthesis of trisubstituted alkenes from alkynes via iodoalkenes using Pd-c