55088-86-3

Upstream product

• 52999-15-2 4-(p-methoxyphenyl)-3-butyn-1-ol 
• 768-60-5 4-methoxyphenylacetylen 
• 74-86-2 acetylene 
• 593-60-2 Vinyl bromide 
• 123-11-5 4-methoxy-benzaldehyde 
• 3989-14-8 (4-methoxyphenylethynyl)trimethylsilane 
• 696-62-8 para-iodoanisole 
• 87639-43-8 4-(4-methoxyphenyl)but-3-yn-1-yl 4-methylbenzenesulfonate 
• 75-89-8 2,2,2-trifluoroethanol 

Downstream Products

• 1201899-31-1 1-phenyl-1-(4'-methoxyphenyl)octa-1,2-diene 
• 1182237-75-7 1-(4-methoxyphenyl)-4-(4-methylphenyl)-3-(trimethylsilyl)but-1-yne 
• 1182237-63-3 1-(4-methoxyphenyl)-4-(4-methylphenyl)-1-(trimethylsilyl)buta-1,2-diene 
• 1060666-94-5 4-methoxy-2'-(phenylethynyl)-1,1':3',1''-terphenyl 

Relevant academic research and scientific papers

Hydromagnesiation of 1,3-Enynes by Magnesium Hydride for Synthesis of Tri- and Tetra-substituted Allenes

A protocol for regio-controlled hydromagnesiation of 1,3-enynes was developed using magnesium hydride that is generated in situ by solvothermal treatment of sodium hydride (NaH) and magnesium iodide (MgI2) in THF. The resulting allenylmagnesium species could be converted into tri- and tetra-substituted allenes by subsequent treatment with various carbon- and silicon-based electrophiles with the aid of CuCN as a catalyst.

Synthesis of α-Alkynylnitrones via Hydromagnesiation of 1,3-Enynes with Magnesium Hydride

A protocol for the synthesis of α-Alkynylnitrones from 1,3-enynes has been developed. The process is triggered by hydromagnesiation of 1,3-enynes with magnesium hydride (MgH2), which is prepared in situ through solvothermal treatment of magnesium iodide (

Stereodivergent Synthesis of Tertiary Fluoride-Tethered Allenes via Copper and Palladium Dual Catalysis

Herein we describe a protocol for the unprecedented stereodivergent synthesis of tertiary fluoride-tethered allenes bearing a stereogenic center and stereogenic axis via Cu/Pd synergistic catalysis. A broad scope of conjugated enynes are coupled with various α-fluoroesters in high yields with high diastereoselectivities and generally >99% ee. In addition, the four stereoisomers of the allene products ensure precise access to the corresponding four stereoisomers of the fluorinated hydrofurans via a novel stereodivergent axial-to-central chirality transfer process.

Regioselective Access to 3-Ethylideneflavanones via Rhodium(I)-Catalyzed 1,3-Enyne Hydroacylation/Annulation Cascades

The highly efficient synthesis of 3-ethylideneflavanones through sequential rhodium(I)-catalyzed hydroacylation of terminal aryl-substituted 1,3-enynes with chelating aldehydes and annulation is described. This straightforward protocol highlights an unprecedented C3-regioselective hydroacylation of 1,3-enynes, excellent functional group compatibility, and complete atom economy. (Figure presented.).

Cobalt-Catalyzed gem-Cross-Dimerization of Terminal Alkynes

Transition-metal-catalyzed dimerization of two different terminal alkynes provides an atom-economic synthesis of valuable conjugated 1,3-enynes. Despite many catalyst systems developed, the state-of-the-art solutions are still limited to special alkynes. A practical catalyst, which could be used to cross-dimerize general aryl alkynes and aliphatic alkynes, is still highly desired. Herein we present the earth-abundant Co(II)-catalyzed highly gem-selective cross-dimerization of aryl alkynes and aliphatic alkynes or gas acetylene under mild reaction conditions. Conjugated 1,3-enynes with various useful functional groups can be prepared in high yields. The application of Co(OAc)2 and t-butyl group substituted triphos ligand is essential to distinguish the alkynes at different steps and realize the gem-selectivity.

Fe-Catalyzed Selective Cyclopropanation of Enynes under Photochemical or Thermal Conditions

The nucleophilic Fe-complex Bu4N[Fe(CO)3(NO)] (TBA[Fe]) catalyzes the cyclopropanation of enynes to substituted propargyl cyclopropanes using diazoesters as carbene surrogates. The catalyst can be activated either thermally in the presence of catalytic amounts of 4-nitroanisole or under photochemical conditions. Cyclopropanation occurs selectively at the enyne moiety; alternative olefinic moieties remain intact.

Enantioselective Synthesis of Multisubstituted Allenes by Cooperative Cu/Pd-Catalyzed 1,4-Arylboration of 1,3-Enynes

A cooperative Cu/Pd-catalyzed enantioselective synthesis of multisubstituted allenes is established. By employing chiral sulfoxide phosphine (SOP)/Cu and PdCl2(dppf) complexes as catalysts, the 1,4-arylboration of 1,3-enynes provides an efficient approach to trisubstituted chiral allenes with up to 92 % yield and 97:3 er. Furthermore, by using 2-substituted 1,3-enynes as substrates, the tetrasubstituted chiral allenes were successfully generated using this strategy. Finally, theoretical calculations indicate that the transmetallation of the allenylcopper species is the rate-limiting step of this transformation.

Direct access to pentenedinitriles: Via Ni-catalyzed dihydrocyanation of 1,3-enynes

A highly regio-and stereoselective dihydrocyanation of 1,3-enynes was implemented by nickel/diphosphine catalysts. This reaction represents the first example of Ni-catalyzed dihydrocyanation of 1,3-enynes using TMSCN and MeOH as HCN surrogates. In this tr

Preparation of Chiral Allenes through Pd-Catalyzed Intermolecular Hydroamination of Conjugated Enynes: Enantioselective Synthesis Enabled by Catalyst Design

In this study, we establish that conjugated enynes undergo selective 1,4-hydroamination under Pd catalysis to deliver chiral allenes with pendant allylic amines. Several primary and secondary aliphatic and aryl-substituted amines couple with a wide range of mono- and disubstituted enynes in a nonenantioselective reaction where DPEphos serves as the ligand for Pd. Benzophenone imine acts as an ammonia surrogate to afford primary amines in a two-step/one-pot process. Examination of chiral catalysts revealed a high degree of reversibility in the C-N bond formation that negatively impacted enantioselectivity. Consequently, an electron-poor ferrocenyl-PHOX ligand was developed to enable efficient and enantioselective enyne hydroamination.

Triple-Bond Insertion Triggers Highly Regioselective 1,4-Aminomethylamination of 1,3-Enynes with Aminals Enabled by Pd-Catalyzed C-N Bond Activation

A highly chemo- and regioselective 1,4-aminomethylamination of simple enynes with aminals to allenic 1,5-diamines by taking advantage of C-N bond activation has been reported. The reaction proceeds under mild reaction conditions and can be performed under