76347-62-1

Upstream product

• 67-64-1 acetone 
• 106-37-6 1.4-dibromobenzene 
• 115-19-5 2-methyl-but-3-yn-2-ol 
• 589-87-7 1,4-bromoiodobenzene 
• 1453814-02-2 1-(((4-(4-bromophenyl)-2-methylbut-3-yn-2-yl)oxy)methyl)-2-nitrobenzene 
• 673-40-5 4-bromobenzenediazonium tetrafluoroborate 
• 106-40-1 4-bromo-aniline 
• 766-96-1 4-bromo-1-ethynylbenzene 

Downstream Products

• 75111-07-8 1-(4-Bromphenyl)-3-chlor-3-methyl-1-butin 
• 500899-32-1 2-methyl-4-(4'-bromophenyl)but-1-en-3-yne 
• 766-96-1 4-bromo-1-ethynylbenzene 
• 75111-13-6 5-<(E)-4-Brom-α-chlorbenzyliden>-6,6-dimethylbicyclo<2.2.1>hept-2-en 
• 167858-39-1 4-(3-hydroxy-3,3-dimethyl-1-propynyl)-1-(1-trans-pentenyl)benzene 
• 1360703-57-6 (Z)-3-benzoyl-4-(4-bromobenzylidene)-5,5-dimethyloxazolidin-2-one 
• 1417574-47-0 1-bromo-4-(3-(4-methoxyphenyl)-3-methylbut-1-ynyl)benzene 
• 141735-23-1 (E)-1-bromo-4-(3-methylbuta-1,3-dien-1-yl)benzene 
• 1453814-02-2 1-(((4-(4-bromophenyl)-2-methylbut-3-yn-2-yl)oxy)methyl)-2-nitrobenzene 
• 2344-53-8 1,4-bis(2-hydroxy-2-methyl-4-but-3-ynyl)benzene 
• 2344-52-7 4-ethynyl-1-(3-hydroxy-3-methyl-1-butynyl)benzene 
• 935-14-8 1,4-diethynylbenzene 
• 1453814-03-3 2-methyl-4-(4-(3-methyl-3-((2-nitrobenzyl)oxy)but-1-yn-1-yl)phenyl)but-3-yn-2-ol 
• 1453814-04-4 1-(((4-(4-ethynylphenyl)-2-methylbut-3-yn-2-yl)oxy)methyl)-2-nitrobenzene 

Relevant academic research and scientific papers

Multicolor Mechanofluorophores for the Quantitative Detection of Covalent Bond Scission in Polymers

The fracture of polymer materials is a multiscale process starting with the scission of a single molecular bond advancing to a site of failure within the bulk. Quantifying the bonds broken during this process remains a big challenge yet would help to understand the distribution and dissipation of macroscopic mechanical energy. We here show the design and synthesis of fluorogenic molecular optical force probes (mechanofluorophores) covering the entire visible spectrum in both absorption and emission. Their dual fluorescent character allows to track non-broken and broken bonds in dissolved and bulk polymers by fluorescence spectroscopy and microscopy. Importantly, we develop an approach to determine the absolute number and relative fraction of intact and cleaved bonds with high local resolution. We anticipate that our mechanofluorophores in combination with our quantification methodology will allow to quantitatively describe fracture processes in materials ranging from soft hydrogels to high-performance polymers.

Rhodium-Catalyzed Annulation of Phenacyl Ammonium Salts with Propargylic Alcohols via a Sequential Dual C-H and a C-C Bond Activation: Modular Entry to Diverse Isochromenones

Given their omnipresence in natural products and pharmaceuticals, isochromenone congeners are one of the most privileged scaffolds to synthetic chemists. Disclosed herein is a dual (ortho/meta) C-H and C-C activation of phenacyl ammonium salts (acylammonium as traceless directing group) toward annulation with propargylic alcohols to accomplish rapid access for novel isochromenones by means of rhodium catalysis from readily available starting materials. This operationally simple protocol features broad substrate scope and wide functional group tolerance. Importantly, the protocol circumvents the need of any stoichiometric metal oxidants and proceeds under aerobic conditions.

Dual Palladium/Copper-Catalyzed anti-Selective Intermolecular Allenylsilylation of Terminal Alkynes: Entry to (E)-Silyl Enallenes

A palladium-/copper-cocatalyzed three-component trans-allenylsilylation of terminal alkynes with propargyl acetates and PhMe2SiBpin is described, which is driven by the regioselective allenylation of the alkyne with propargyl acetates and then silylation. This method allows the simultaneous incorporation of an allene and silicon across the CC bond and provides a highly chemo-, regio-, and stereoselective alkyne difunctionalization route to the synthesis of valuable (E)-silyl enallenes. The utility of this method is highlighted by late-stage derivatization of bioactive compounds.

Utilizing a copper-free Sonogashira reaction in the synthesis of the leukotriene a4 hydrolase modulator batatasin IV

Batatasin IV is a dihydrostilbenoid isolated from Chinese yams which was shown to have inhibitory activities against plant growth. Later studies showed that this compound may exhibit anti-inflammatory properties by inhibiting the epoxide hydrolase activity of the leukotriene A4 hydrolase enzyme. To access the dihydrostilbenoid skeleton, a copper-free SPhos-mediated Sonogashira reaction was conceived and the substrate scope was explored. Our results indicate that the reaction can tolerate the presence of free alcohols, aldehydes, nitro groups, and anilinyl groups. However, a substituent with an acidic phenol or carboxylic acid group gave significantly lower yields. Next, a total synthesis of batatasin IV was accomplished in 16% overall yield incorporating the reported copper-free Sonogashira reaction. Finally, we show that batatasin IV inhibits the hydrolysis of alanine p-nitroanilide by leukotriene A4 hydrolase with an IC50 of 91.4 μM.

Palladium(II)/Lewis acid cocatalyzed oxidative annulation of 2-alkenylanilines and propargylic esters: An access to benzo[ b]azepines

An attractive approach to valuable yet synthetically challenging benzo[b]azepines was established via palladium(II)/Lewis acid cocatalyzed oxidative [5 + 2] annulation of readily available 2-alkenylanilines and propargylic esters. The protocol features mild reaction conditions and good functional group tolerance, constituting an array of benzo[b]azepines in yields of 30-75%.

Visible-light-driven selective alkenyl C-P bond cleavage of allenylphosphine oxides

An efficient method for highly selective alkenyl C-P bond cleavage, enabled by organic dyes and visible-light irradiation, was developed. This novel protocol involves a highly regioselective radical pathway initiated by singlet oxygen, affording diverse a

DBU-promoted carbonylative synthesis of 1,3-oxathiolan-2-ones from propargylic alcohols with TFBen as the CO source

A DBU-promoted carbonylative cyclization of propargylic alcohols with sulfur was developed. Various 1,3-oxathiolan-2-ones were produced in 61-98% yields under mild conditions in the absence of metal catalysts. TFBen (benzene-1,3,5-triyl triformate) as an efficient and solid CO surrogate and S8 as an ideal sulfur source were employed and incorporated.

Highly Efficient Synthesis of Multi-Substituted Allenes from Propargyl Acetates and Organoaluminum Reagents Mediated by Palladium

A simple and mild catalytic S N 2′ substitution reaction of propargyl acetates with organoaluminum reagents is reported. The S N 2′ substitution reaction of propargyl acetates with organoaluminum reagents mediated by Pd(PhP 3) 2 Cl 2 (1 mol%)/PPh 3 (2 mol%)/K 2 CO 3 in tetrahydrofuran at 60 °C for 3-4 hours afforded the corresponding multi-substituted allenes in good yields (up to 94%) with high selectivities (up to 99%). The process was simple and easily performed, which offers an efficient method to synthesize the multi-substituted allene derivatives.

Synthesis and Photochemistry of a New Photolabile Protecting Group for Propargylic Alcohols

A new and efficient thiochromenone S,S-dioxide-based photolabile protecting group for propargylic alcohols is described. Robust protection reactions were developed through copper (II)-catalyzed substitution of propargylic alcohols. Subsequent photodeprote

Ligand-Assisted Gold-Catalyzed Cross-Coupling with Aryldiazonium Salts: Redox Gold Catalysis without an External Oxidant

Gold-catalyzed C(sp)-C(sp2) and C(sp2)-C(sp2) cross-coupling reactions are accomplished with aryldiazonium salts as the coupling partner. With the assistance of bpy ligand, gold(I) species were oxidized to gold(III) by diazonium without any external oxidants. Monitoring the reaction with NMR and ESI-MS provided strong evidence for the nitrogen extrusion followed by AuIII reductive elimination as the key step.