690211-19-9

Upstream product

• 593-60-2 Vinyl bromide 
• 937-31-5 (4-Nitrophenyl)acetylene 
• 555-16-8 4-nitrobenzaldehdye 
• 74-86-2 acetylene 
• 247129-85-7 (2-bromoethyl)(diphenyl)sulfonium trifluoromethanesulfonate 

Downstream Products

• 931429-19-5 (+/-)-2-[(4-nitrophenyl)ethynyl]oxirane 

Relevant academic research and scientific papers

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.).

Pd/Cu-Catalyzed Vinylation of Terminal Alkynes with (2-Bromoethyl)diphenylsulfonium Triflate

The potential of (2-bromoethyl)diphenylsulfonium triflate to be a powerful vinylation reagent was determined by the Sonogashira cross-coupling reactions with terminal alkynes. The vinylation proceeded smoothly at 25 °C under Pd/Cu catalysis to afford a variety of 1- and 2-unsubstituted 1,3-enynes in moderate to excellent yields. This protocol represents the first application of (2-haloethyl)diphenylsulfonium triflate as a CH═CH2 transfer source in organic synthesis.

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.

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.

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

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

Convenient access to functionalized vinylcyclopentenols from alkynyloxiranes

β,γ-Alkynyl aldehydes, generated in situ by treatment of alkynyloxiranes with a catalytic amount of Sc(OTf)3 or BF 3· OEt2, are effectively trapped by a variety of allyl nucleophiles to afford homopropargylic homoallylic a