33622-26-3

Upstream product

• 689-97-4 3-buten-1-yne 
• 593-60-2 Vinyl bromide 
• 629-05-0 n-octyne 
• 60212-31-9 Undec-4-in 
• 1188-92-7 Trihexylboran; Tri-n-hexylbor 
• 16356-02-8 1,4-dimethoxy-2-butyne 
• 5921-74-4 1-bromo-2-nonyne 
• 47025-43-4 methylenetriphenylarsorane 
• 64-17-5 ethanol 
• 1092482-79-5 Br^(1-)*C₂₈H₃₂P⁽¹⁺⁾ 
• 55682-66-1 deca-1,3-diyne 

Downstream Products

• 88687-87-0 2-Hexyl-1,1,1,6,6,6-hexaphenyl-hexadien-(2,3) 
• 214552-98-4 2-vinyl-1,3-terphenyl 
• 820964-84-9 (C₄H₉)3SnC₆H₂(C₆H₁₃)2CHCH₂ 
• 1204834-42-3 2,2-dimethyl-6-(phenylmethyl)-dodeca-4,5-diene 

Relevant academic research and scientific papers

Radical Carbonyl Propargylation by Dual Catalysis

Carbonyl propargylation has been established as a valuable tool in the realm of carbon–carbon bond forming reactions. The 1,3-enyne moiety has been recognized as an alternative pronucleophile in the above transformation through an ionic mechanism. Herein, we report for the first time, the radical carbonyl propargylation through dual chromium/photoredox catalysis. A library of valuable homopropargylic alcohols bearing all-carbon quaternary centers could be obtained by a catalytic radical three-component coupling of 1,3-enynes, aldehydes and suitable radical precursors (41 examples). This redox-neutral multi-component reaction occurs under very mild conditions and shows high functional group tolerance. Remarkably, bench-stable, non-toxic, and inexpensive CrCl3 could be employed as a chromium source. Preliminary mechanistic investigations suggest a radical-polar crossover mechanism, which offers a complementary and novel approach towards the preparation of valuable synthetic architectures from simple chemicals.

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.

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

Divergent Synthesis of CF3-Substituted Allenyl Nitriles by Ligand-Controlled Radical 1,2- and 1,4-Addition to 1,3-Enynes

A ligand-controlled system that enables regioselective trifluoromethylcyanation of 1,3-enynes has been identified, which provides access to a variety of CF3-containing tri- and tetrasubstituted allenyl nitriles. We disclose that the involved propargylic radicals can be selectively trapped by (Box)CuII cyanide, while the tautomerized allenyl radicals are trapped by (phen)CuII cyanide (Box= bisoxazoline, phen=phenanthroline). In addition, the reaction features broad substrate scope and excellent functional group compatibility. Moreover, this protocol represents a novel regioselectivity-tunable functionalization of 1,3-enynes via radicals, which we believe will have great implications for the development of catalytic systems for selectivity control in radical and organometallic chemistry.

Copper-catalyzed silylation reactions of propargyl epoxides: Easy access to 2,3-allenols and stereodefined alkenes

Efficient silylation reactions of propargyl epoxides catalyzed by copper catalysts have been developed. Under mild reaction conditions, tri- and tetra-substituted functionalized allenols and alkenes could be selectively obtained in moderate to high yields

Synthesis of cyclobutenes and allenes by cobalt-catalyzed cross-dimerization of simple alkenes with 1,3-enynes

Cobalt-catalyzed cross-dimerization of simple alkenes with 1,3-enynes is reported. A [2+2] cycloaddition reaction occurred, with alkenes bearing no allylic hydrogen, by reductive elimination of a η3-butadienyl cobaltacycle. On the other hand, a

Regioselective solvent-dependent benzannulation of conjugated enynes

The transformation of enynes under cobalt-catalysis leads to symmetrical benzannulation products in dichloromethane. In tetrahydrofuran the cobalt-catalysed reactions afforded the unprecedented unsymmetrical benzannulation products in moderate to good yields and good regioselectivities. In addition, cyclotrimerisation of the alkyne subunit can be realised when electron-deficient enynes are applied in the cobalt-catalysed transformations to generate 1,2,4-trivinylbenzene derivatives using tetrahydrofuran as solvent.

Silver-catalyzed carbomagnesiation of terminal aryl and silyl alkynes and enynes in the presence of 1,2-dibromoethane

Regioselective carbomagnesiation of terminal alkynes and enynes with alkyl Grignard reagents has been achieved by the combined use of a silver catalyst and 1,2-dibromoethane. The Royal Society of Chemistry 2009.