71832-03-6

Upstream product

• 591-51-5 phenyllithium 
• 1896-62-4 (E)-benzalacetone 
• 591-50-4 iodobenzene 
• 917-54-4 methyllithium 
• 614-47-1 1,3-diphenyl-propen-3-one 
• 75-16-1 methylmagnesium bromide 
• 1088-02-4 triphenylgallane 
• 127-66-2 2-Phenyl-3-butyn-2-ol 
• 108-86-1 bromobenzene 
• 94-41-7 benzalacetophenone 
• 108162-13-6 Z-styryl n-butyltelluride 
• 100-52-7 benzaldehyde 
• 98-86-2 acetophenone 
• 98-80-6 phenylboronic acid 

Downstream Products

• 109807-72-9 (+/-)-3ξ,5-diphenyl-cyclohex-4-ene-1r,2c-dicarboxylic acid-anhydride 
• 1636897-05-6 1-{4,5-dihydro-2,5-diphenyl-5-[ (E)-2-phenylethenyl]furan-3-yl}ethanone 
• 22360-63-0 1-Phenyl-3-methylindene 
• 1354701-49-7 (E)-(3-azidobut-1-ene-1,3-diyl)dibenzene 
• 1375748-77-8 C₁₆H₁₅N₃ 

Relevant academic research and scientific papers

Selective Aerobic Oxygenation of Tertiary Allylic Alcohols with Molecular Oxygen

Aerobic epoxidation of tertiary allylic alcohols remains a significant challenge. Reported here is an efficient and highly chemoselective copper-catalyzed epoxidation and semipinacol rearrangement reaction of tertiary allylic alcohols with molecular oxygen. The solvent 1,4-dioxane activates dioxygen, thereby precluding the addition of a sacrificial reductant.

Synthesis, characterization, and investigations of antimicrobial activity of benzopyrans, benzofurans and spiro[4.5]decanes

In this study, the radical cyclization reactions of cyclic 1,3-dicarbonyl compounds (1a–c) and α,β-unsaturated alcohols (2a–d) through Mn(OAc)3 were performed. A series of biologically interesting dihydropyrans (3–5) and dihydrofurans (6–18) were synthesized as a result of these reactions. Spiro compounds (19–20) were obtained from the reactions of 1,3-dicarbonyl compounds and (E)-2,4-diphenyl-but-3-en-2-ol (2e). The unique structure of compound 19 was also confirmed by X-ray crystallography. In addition, the antibacterial activities of synthesized compounds were screened against some bacteria. Their zone diameters showed better results than some known antibiotics.

Ni-Catalyzed regio- and stereoselective addition of arylboronic acids to terminal alkynes with a directing group tether

Addition of arylboronic acids to directing group tethered acetylenes in a regio and stereoselective manner using an inexpensive catalytic system is achieved for the first time to access highly sought after allyl/homoallyl alcohol/amine units. The apparent vinylnickel intermediate was successfully trapped by the Michael electrophiles to get defined tri- and tetra-substituted olefins. An interesting selectivity switch was observed with internal alkynes.

Catalytic Enantioselective Addition of Aryl Grignard Reagents to Ketones

We report a catalytic system for the challenging enantioselective addition of aryl Grignard reagents to ketones. Using a simple, one-pot procedure under mild conditions, a wide range of aromatic ketones are converted into diaryl alcohols in good yields and with good enantioselectivities. The catalytic enantioselective addition of aryl Grignard reagents to ketones is now possible. Using a readily available Ar-BINMOL ligand and titanium(IV) isopropoxide in a simple, one-pot procedure under mild conditions, a wide range of aromatic ketones are converted into diaryl alcohols in good yields and with good enantioselectivities.

Synthesis of dihydropyrans and dihydrofurans via radical cyclization of unsaturated alcohols and 1,3-dicarbonyl compounds

The oxidative cyclization reactions of 1,3-dicarbonyl compounds 1a-1c and α,β-unsaturated alcohols 2a-2f with Mn(OAc)3 were performed, leading to dihydrofurans. Treatment of 1a and 1b with 2-methylbut-3-en-2-ol (2a) gave dihydrofurans 3aa and 3ba, and dihydropyrans 4aa and 4ba, as unexpected products. While the reaction of 2-methylbut-3-yn-2-ol (2b) with acetylacetone (1b) yielded a bifuran, ethyl acetoacetate (1a) led to a mixture of furan, bifuran, and salicylate derivatives. Besides, surprisingly, styryl-substituted dihydrofurans were obtained from the reactions of 1,3-dicarbonyl compounds and (3E)-2,4-diphenylbut-3-en-2-ol. The reaction mechanisms were proposed for the formation of the different products, considering intermediates in these reaction mixtures. Copyright

Lithium choreography: Intramolecular arylations of carbamate-stabilised carbanions and their mechanisms probed by in situ IR spectroscopy and DFT calculations

Deprotonation of O-allyl, O-propargyl or O-benzyl carbamates in the presence of a lithium counterion leads to carbamate-stabilised organolithium compounds that may be quenched with electrophiles. We now report that when the allylic, propargylic or benzylic carbamate bears an N-aryl substituent, an aryl migration takes place, leading to stereochemical inversion and C-arylation of the carbamate α to oxygen. The aryl migration is an intramolecular S NAr reaction, despite the lack of anion-stabilising aryl substituents. Our in situ IR studies reveal a number of intermediates along the rearrangement pathway, including a "pre-lithiation complex," the deprotonated carbamate, the rearranged anion, and the final arylated carbamate. No evidence was obtained for a dearomatised intermediate during the aryl migration. DFT calculations predict that during the reaction the solvated Li cation moves from the carbanion centre, thus freeing its lone pair for nucleophilic attack on the remote phenyl ring. This charge separation leads to several alternative conformations. The one having Li+ bound to the carbamate oxygen gives rise to the lowest-energy transition structure, and also leads to inversion of the configuration. In agreement with the IR studies, the DFT calculations fail to locate a dearomatised intermediate. Dancing to lithium's tune: In situ IR spectroscopy and DFT calculations allow the detailed pathways of aryl migrations taking place in lithiated carbamates to be characterised (see scheme).

A new approach to organomanganese compounds: The tellurium/manganese exchange reaction

Diorganomanganese compounds react with aryl, vinyl, and alkynyl tellurides in a tellurium/manganese exchange reaction. The new mixed organomanganese reagents react selectively with electrophiles.

New and efficient synthesis of solid-supported organotin reagents and their use in organic synthesis

Novel resin-bound organotin reagents have been prepared, including for the first time resin-bound dimethyl tin reagents. Mild methodology has also been developed for the very efficient synthesis of resin-bound distannanes. The resin-bound tin chloride rea

Effect of InCl3 on the addition of Grignard reagents to α,β-unsaturated carbonyl compounds

Control of 1,2- versus 1,4-addition of organometallic reagents to enones remains a long-standing problem. There is still no satisfactory 1,2-directing agent comparable to the 1,4-directing effect of copper salts. We report that the presence of just 5 mol% indium(III) chloride can significantly alter the amount of 1,2-product formed in these reactions.

Tetraorganogallate complexes in organic chemistry: Michael addition to α, β-unsaturated compounds

Tetraorganogallate complexes, prepared in situ by addition of an organolithium reagent to a triorganogallium, reacted smoothly with α,β- unsaturated compounds to give Michael addition products in high yields, and mixed gallates display very high chemoselectivity in the transfer of one of their ligands.