170859-77-5

Upstream product

• 35779-04-5 1-tert-butyl-4-iodobenzene 
• 107-19-7 propargyl alcohol 
• 3972-65-4 1-bromo-4-tert-butylbenzene 
• 50-00-0 formaldehyd 
• 772-38-3 4-tert-Butylphenylacetylene 

Downstream Products

• 1367053-87-9 (R)-2-(4-tert-butylphenyl)-4-(nitromethyl)-4H-chromene-3-carbaldehyde 

Relevant academic research and scientific papers

Bi(OTf)3-catalyed One-pot Synthesis of α-Halo-β-amino Ketones and Acyl Aziridines from 3-Aryl Propargyl Alcohols

A Bi(OTf)3-catalyed reaction of 3-aryl propargyl alcohols with sulfonamide and halogen source was firstly investigated, which provided a facile route for the synthesis of a large variety of α-halo-β-amino ketones. The key intermediates, β-amino

Copper-Catalyzed Cross-Nucleophile Coupling of β-Allenyl Silanes with Tertiary C-H Bonds: A Radical Approach to Branched 1,3-Dienes

Described herein is a distinctive approach to branched 1,3-dienes through oxidative coupling of two nucleophilic substrates, β-allenyl silanes, and hydrocarbons appending latent functionality by copper catalysis. Notably, C(sp3)-H dienylation proceeded in a regiospecific manner, even in the presence of competitive C-H bonds that are capable of occurring hydrogen atom transfer process, such as those located at benzylic and other tertiary sites, or adjacent to an oxygen atom. Control experiments support the intermediacy of functionalized alkyl radicals.

3-aryl-2-propyn-1-ol derivative and preparation method thereof

The invention discloses a 3-aryl-2-propyn-1-ol derivative and a preparation method thereof, belongs to the field of organic synthesis, and particularly relates to a 3-aryl-2-propyn-1-ol derivative anda preparation method thereof. A purpose of the invention is to solve the problems of high energy consumption, high cost and environmental pollution caused by conditions of high temperature, metal catalysis, strong base or low temperature and the like required by the synthesis of the existing 3-aryl-2-propyn-1-ol derivative. The structural formula of the 3-aryl-2-propyn-1-ol derivative is shown inthe specification. The method comprises the following steps: 1, sequentially adding an aryl acetylene compound, an ammonium salt, an alkali, water and an organic solvent into a three-necked flask, and electrolyzing at room temperature in an air atmosphere under a stirring condition; 2, extracting, and carrying out reduced pressure distillation to remove the solvent to obtain a crude product; and3, purifying the crude product through silica gel column chromatography to obtain the 3-aryl-2-propyn-1-ol derivative. According to the invention, the 3-aryl-2-propyn-1-ol derivative can be obtained.

Catalyst-Free Annulation of 2-Pyridylacetates and Ynals with Molecular Oxygen: An Access to 3-Acylated Indolizines

A catalyst and additive-free annulation of 2-pyridylacetates and ynals under molecular oxygen was the first developed, affording 3-acylated indolizines in good to excellent yields. Molecular oxygen was used as the source of the carbonyl oxygen atom in indolizines. This approach was compatible with a wide range of functional groups, and especially it has been successfully extended to unsaturated double bonds and triple bonds, which were difficult to prepare by previous methods in a single step.

Metal-free aminothiation of alkynes: Three-component tandem annulation toward indolizine thiones from 2-alkylpyridines, ynals, and elemental sulfur

A metal-free three-component annulation reaction for the synthesis of indolizine thiones via tandem C-C/C-N/C-S bond formation was developed. Various 2-alkylpyridines with aromatic ynals and elemental sulfur proceeded smoothly under catalyst-free conditions, and the desired products were obtained in moderate to excellent yields.

Synthesis of N-Heterocycles-Fused Azasilines by Palladium-Catalyzed Si-Si Bond Activation

Azasilines fused nitrogen heterocycles are prepared in excellent yields (from 74 to 98 % according to the structures) for the first time in one operation with high regio- and stereoselectivities. The key step consists of an intramolecular palladium-cataly

Catalytic asymmetric synthesis of 2,5-dihydrofurans using synergistic bifunctional Ag catalysis

We report a bifunctional Ag catalyst promoted intramolecular capture of oxonium ylides with alkynes for the enantioselective synthesis of 2,5-dihydrofurans. This represents unprecedented synergistic catalysis of a bifunctional Ag catalyst. Mechanistic studies revealed that [(R)-3,5-DM-BINAP](AgSbF6)2 (9) is likely to be the active catalytic species and that the reaction involves second order kinetics with respect to 9, suggesting that two molecules of 9 are involved in the intramolecular trapping of a Ag-associated oxonium ylide with a Ag-activated alkyne. Based on our mechanistic hypothesis, we further optimized the reaction, rendering a facile approach to 2,5-dihydrofurans in good to excellent yields in a highly chemo- and enantioselective fashion.

Nickel(II)-Catalyzed Asymmetric Propargyl [2,3] Wittig Rearrangement of Oxindole Derivatives: A Chiral Amplification Effect

A highly enantioselective [2,3] Wittig rearrangement of oxindole derivatives was realized by using a chiral N,N′-dioxide/NiII complex as the catalyst under mild reaction conditions. A strong chiral amplification effect was observed, and allowed access to chiral 3-hydroxy 3-substituted oxindoles bearing allenyl groups in high yields and enantioselectivities (up to 92 % ee) by using a ligand with only 15 % ee. A reasonable explanation was given based on the experimental investigations and X-ray crystal structures of enantiomerically pure and racemic catalysts. Moreover, the first catalytic kinetic resolution of racemic oxindole derivatives by a [2,3] Wittig rearrangement was realized with high efficiency and stereoselectivity.

Expedient synthesis of new cinnoline diones by Ru-catalyzed regioselective unexpected deoxygenation-oxidative annulation of propargyl alcohols with phthalazinones and pyridazinones

Ruthenium-catalyzed simple, cascade and one-pot synthesis of cinnoline-fused diones has been carried out by the C-H activation of phthalazinones/pyridazinones accomplished by the unusual deoxygenation of propargyl alcohols. The bond selectivity is accredited to the traceless directing nature of the hydroxyl group of propargyl alcohol. A sequential C-H activation, insertion and deoxy-oxidative annulation has been proposed based on the preliminary mechanistic study.

A gold(i)-catalyzed substituent-controlled cycloisomerization of propargyl vinyl ethers to multi-substituted furofuran and furopyran derivatives

A gold(i)-catalyzed substituent-controlled strategy for the stereoselective synthesis of bicyclic furan and pyran derivatives has been developed. The mechanisms of the reactions have been studied thoroughly by deuterium labelling experiments. The applications of the methodologies were demonstrated by evaluating the preliminary anti-fungal activity of the synthetic compounds.