119379-68-9

Upstream product

• 501-65-5 diphenyl acetylene 
• 591-50-4 iodobenzene 
• 536-74-3 phenylacetylene 
• 264144-59-4 (Z)-1-(4',4',5',5'-tetramethyl-1’,3’,2’-dioxaborolan-2’-yl)-1,2-diphenylethene 
• 91-47-4 2,3-diphenylacrylic acid 

Downstream Products

• 1233-23-4 (E)-1-(4-methoxyphenyl)-1,2-diphenylethylene 
• 156181-20-3 (Z)-1,1'-(1-Iodo-1,2-ethenediyl)bisbenzene 
• 5925-58-6 (E)-1-(1-naphthyl)-1,2-diphenylethene 
• 72474-41-0 cis-1,2-diphenyl-1-(p-hydroxyphenyl) ethylene 
• 97800-39-0 cis-1,2-diphenyl-1-<4-(2-diethylaminoethoxy)phenyl>ethylene 
• 136409-34-2 N-(1,2-Diphenylvinyl)-2,2-diphenylacetamid 
• 1283735-48-7 (R,E)-1,2,3-triphenylprop-2-en-1-ol 
• 57015-16-4 (E)-1,2,3-triphenylprop-2-en-1-ol 
• 1256779-10-8 (E)-1-cyclohexyl-2,3-diphenylprop-2-en-1-ol 
• 1283735-49-8 (E)-1-cyclohexyl-2,3-diphenylprop-2-en-1-ol 
• 56162-82-4 3,4,5-triphenyl-pyrrole-2-carboxylic acid 
• 1567951-21-6 C₃₂H₂₇NO₃ 
• 1567951-26-1 C₂₄H₂₁NO 
• 3947-92-0 1-deutero-cis-1,2-diphenylethylene 

Relevant academic research and scientific papers

Palladium-Catalyzed Decarbonylative Iodination of Aryl Carboxylic Acids Enabled by Ligand-Assisted Halide Exchange

We report an efficient and broadly applicable palladium-catalyzed iodination of inexpensive and abundant aryl and vinyl carboxylic acids via in situ activation to the acid chloride and formation of a phosphonium salt. The use of 1-iodobutane as iodide source in combination with a base and a deoxychlorinating reagent gives access to a wide range of aryl and vinyl iodides under Pd/Xantphos catalysis, including complex drug-like scaffolds. Stoichiometric experiments and kinetic analysis suggest a unique mechanism involving C?P reductive elimination to form the Xantphos phosphonium chloride, which subsequently initiates an unusual halogen exchange by outer sphere nucleophilic substitution.

Regio- And Stereoselective Hydroiodination of Internal Alkynes with Ex Situ-Generated HI

Herein, we report an efficient and practical hydroiodination of internal alkynes using HI generated ex situ from the readily available triethylsilane and I2. This system offers high regio- and stereoselectivity to afford (E)-vinyl iodides in good yields under mild conditions. Furthermore, the hydroiodination reaction shows high functional group tolerance toward alkyl, methoxy, halogen, trifluoromethyl, cyano, ester, halomethyl, acid-sensitive silyl ether, and acetal moieties.

Visible light-mediated metal-free double bond deuteration of substituted phenylalkenes

Various bromophenylalkenes were reductively photodebrominated by using 1,3-dimethyl-2-phenyl-1H-benzo-[d]imidazoline (DMBI) and 9,10-dicyanoanthracene. With deuterated DMBI analogs (the most effective was DMBI-d11), satisfactory to excellent isotopic yields were obtained. DMBI-d11 could also be regenerated from the reaction mixtures with a recovery rate of up to 50%. The combination of the photodebromination reaction with conventional methods for bromoalkene synthesis enables sequential monodeuteration of a double bond without the necessity of a metal catalyst. This journal is

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.

Activation of vinyl iodides for the highly enantioselective addition to aldehydes

(Chemical Equation Presented) Mild and tolerant: Vinylzinc reagents were directly prepared from the reaction of vinyl iodides with ZnEt2 under mild reaction conditions. The compound (S)-1 was found to catalyze the addition of the vinylzinc reag

Palladium-catalyzed stereoselective synthesis of E- and Z-1,1-diaryl or triarylolefins

A stereoselective and flexible synthesis of various E- and Z-1,1-diaryl and triarylolefins 3 was achieved from readily available vinylstannanes 1 via stereospecific iodo-destannylation and subsequent palladium-catalyzed Negishi-type cross-coupling reaction with arylzinc reagents under mild conditions.

Surface-Mediated Reactions. 4. Hydrohalogenation of Alkynes

The use of appropriately prepared silica gel and alumina has been found to mediate the addition of hydrogen halides to alkynes.The technique has been rendered even more convenient by the use of various organic and inorganic acid halides that react in the presence of silica gel or alumina to generate hydrogen halides in situ.Treatment in this fashion of 1-propynylbenzene (1), which underwent no reaction in CH2Cl2 solution saturated with HCl, readily afforded the syn addition product, alkenyl chloride (E)-4a.On extended treatment (E)-4a underwent subsequent iaomerization to the thermodynamically more stable Z isomer.Thus either isomer of 4a could be obtained in good yield depending on the reaction conditions.In a similar way bromides (E)- and (Z)-4b were obtained without competing formation of the radical products (E)- and (Z)-5, which occurred in solution.In contrast with solution-phase hydroiodination of alkyne 1, which slowly afforded iodide (E)-4c, surface-mediated addition readily afforded (E)-4c, followed by isomerization to the Z isomer.E ->/- Z equilibration of the alkenyl halides 4 was shown to involve, at last in part, addition-elimination via the gem-dihalides 13.Analogous behavior was exhibited by the phenylalkynes 2 and 3 on surface-mediated hydrohalogenation.Surface-mediated addition of HBr and HI to the internal alkylalkyne 14 afforded principally the anti addition products (Z)-15b,c.Treatment of the terminal alkynes 17 and 22 with (COBr)2 over alumina gave the dibromides 20 and 24/25, respectively, whereas use of acetyl bromide as the HBr precursor afforded the alkenyl bromides 18b and 23.

Synthesis of Clomid Using Palladium-Catalysed Cross-Coupling

Two methods of choice for the synthesis of clomid, a tetrasubstituted olefin with antiestrogenic activity, are described.The key reaction is hydroalumination of diphenylacetylene followed by C-C cross-coupling using catalytic amount of Pd0.