58672-84-7

Upstream product

• 515129-88-1 2-(deca-1,3-diynyl)aniline 
• 98-86-2 acetophenone 
• 629-05-0 n-octyne 
• 4545-21-5 acetophenone p-toluenesulfonylhydrazone 
• 536-74-3 phenylacetylene 
• 38761-67-0 1-bromo-1-octyne 
• 159087-45-3 4,4,5,5-tetramethyl-2-phenylethynyl-[1,3,2]dioxaborolane 
• 591-50-4 iodobenzene 
• 64531-26-6 1-chloro-1-octyne 
• 1066-54-2 trimethylsilylacetylene 
• 932-87-6 1-Bromo-2-phenylacetylene 
• 81438-46-2 1-iodooct-1-yne 
• 932-88-7 1-iodo-2-phenylethyne 
• 313343-89-4 (E)-1-bromo-1-decene-3-yne 

Downstream Products

• 110792-92-2 (Z)-(dec-3-en-1-ynyl)benzene 
• 126014-45-7 (Z)-(dec-1-en-3-ynyl)benzene 
• 1169837-13-1 [(3Z)-4-(phenylsulfanyl)dec-3-en-1-ynyl]benzene 
• 1422144-22-6 5-benzyl-3-hexyl-1H-pyrazole 
• 1374219-54-1 5-benzyl-3-hexylisoxazole 
• 1092075-04-1 (E)-2-hexyl-1-(4-methoxyphenyl)-5-phenylpent-2-en-4-yn-1-ol 
• 1092075-05-2 (E)-1-(4-methoxyphenyl)-2-phenylundec-2-en-4-yn-1-ol 

Relevant academic research and scientific papers

Stereoselective Synthesis of Highly Substituted Conjugated Dienes via Pd-Catalyzed Carbonylation of 1,3-Diynes

The stereoselective synthesis of conjugated dienes was realized for the first time via Pd-catalyzed alkoxycarbonylation of easily available 1,3-diynes. Key to success is the utilization of the specific ligand 1,1′-ferrocenediyl-bis(tert-butyl(pyridin-2-yl)phosphine) (L1), which allows this novel transformation to proceed at room temperature. A range of 1,2,3,4-tetrasubstituted conjugated dienes are obtained in this straightforward access in high yields and selectivities. The synthetic utility of the protocol is showcased in the concise synthesis of several important intermediates for construction of natural products rac-cagayanin, rac-galbulin, rac-agastinol, and cannabisin G.

Facile Synthesis of Surface-Clean Monodispersed CuOx Nanoparticles and Their Catalytic Properties for Oxidative Coupling of Alkynes

We show a facile method to prepare surface-clean monodispersed small and stable CuOx nanoparticles with controllable average sizes from below 1 nm up to ～5 nm without using bulk capping agent. Structural and surface characterizations show that the chemica

Mesoporous Copper/Manganese Oxide Catalyzed Coupling of Alkynes: Evidence for Synergistic Cooperative Catalysis

Copper oxide supported on mesoporous manganese oxide (meso Cu/MnOx) was synthesized by an inverse micelle templated evaporation induced self-assembly procedure. Controlled aggregation of nanoparticles and a monomodal size distribution of mesopores with tunable structural properties were observed. The material possessed superior catalytic activity in the aerobic oxidative coupling of terminal alkynes. Excellent conversion (>99% in most cases) and selectivity were observed in both homocoupling and cross-coupling of alkynes using the optimized reaction conditions. Use of air as the sole oxidant, avoidance of any kind of additives, ease of product separation, great functional group tolerability, wide synthetic scope, and superior reusability (up to eighth cycle) are the notable features of our catalytic protocol. While the reaction mechanism was elucidated, a synergistic cooperative effect between the copper and manganese has been established, which is responsible for the superior catalytic activity. The labile lattice oxygen of the meso Cu/MnOx played a vital role in deprotonation of the alkyne proton, as supported by TPD and TGA studies. Moreover, for the first time, we designed model complexes for the active sites of the catalyst by DFT calculations and provided a qualitative description of the coupling mechanism, which supports the experimental findings.

Copper(II)-Promoted, One-Pot Conversion of 1-Alkynes with Anhydrides or Primary Amines to the Respective 2,5-Disubstituted Furans or Pyrroles under Microwave Irradiation Conditions

Furans and pyrroles are prepared from 1-alkynes by using a Cu(II)-promoted, one-pot, microwave irradiation method. Glaser coupling of 1-alkynes and cyclization of the resulting 1,3-diyne in the presence of an anhydride or a primary amine results in the formation of the respective 2,5-diaryl- or 2,5-dialkyl-substituted furans and pyrroles.

Copper-catalyzed aerobic oxidative transformation of ketone- Derived N-tosyl hydrazones: An entry to alkynes

A novel strategy involving Cu-catalyzed oxidative transformation of ketone-derived hydrazone moiety to various synthetic valuable internal alkynes and diynes has been developed. This method features inexpensive metal catalyst, green oxidant, good functional group tolerance, high regioselectivity and readily available starting materials. Oxidative deprotonation reactions were carried out to form internal alkynes and symmetrical diynes. Cross-coupling reactions of hydrazones with halides and terminal alkynes were performed to afford functionalized alkynes and unsymmetrical conjugated diynes. A mechanism proceeding through a Cu-carbene intermediate is proposed for the CC triple bond formation.

Cu-catalyzed Fe-driven Csp-Csp and C sp-Csp2 cross-coupling: An access to 1,3-diynes and 1,3-enynes

An efficient Csp-Csp cross-coupling of alkynyl bromide and pinacol ester of alkynyl boronic acid catalyzed by CuFe 2O4 nanoparticles has been accomplished in dimethyl carbonate to produce unsymmetric 1,3-diynes. This protocol is also extended for the Csp-Csp2 coupling of alkynyl bromide and alkenyl boronic acid to provide conjugated 1,3-enynes. The aliphatic, aromatic, and heteroaromatic alkynes couple with various substituted alkynyl/alkenyl boronates/boronic acids by this procedure to furnish a library of 1,3-diynes and enynes in high yields. The catalyst was easily separated by an external magnet and recycled 10 times.

A co-operative Ni-Cu system for Csp-Csp and Csp-Csp2 cross-coupling providing a direct access to unsymmetrical 1,3-diynes and en-ynes

An efficient cross-coupling of alkynes with alkynyl and alkenyl halides catalysed by a Ni-Cu system without any ligand has been achieved. The reaction is suggested to proceed by Ni(0) catalysis assisted by Cu(i). A series of functionalised diaryl, aryl-alkyl, aryl-heteroaryl, diheteroaryl 1,3-di-ynes and en-ynes are obtained in high yields.

Unsymmetrical coupling of 1-chloroalkynes and terminal alkynes under experimental Sonogashira conditions

The coupling of a 1-chloroalkyne and a terminal alkyne to furnish a 1,3-butadiyne under experimental Sonogashira conditions is investigated. Through competition experiments, it is found that 1-chloroalkynes provide cross-coupling products as efficiently (or slightly better) in comparison with iodobenzenes, and almost as effectively as vinyl bromides. Yet, in regard to the degree of conversion into various products, chloroalkynes are the most reactive of all the substrates examined under the explored conditions. Optimized conditions for this cross-coupling reaction are presented. Georg Thieme Verlag Stuttgart New York.

Copper(I) iodide catalyzed cross-coupling reaction of terminal alkynes with 1-bromoalkynes: A simple synthesis of unsymmetrical buta-1,3-diynes

A simple synthesis of unsymmetrical buta-1,3-diynes by cross-coupling of terminal alkynes with 1-bromoalkynes in the presence of copper(I) iodide and tris(o-tolyl)phosphine was developed that gives good yields under simple and mild reaction conditions. The scope and limitations of the cross-coupling reaction were investigated. Georg Thieme Verlag Stuttgart · New York.

Transition-metal-free homocoupling of 1-haloalkynes: A facile synthesis of symmetrical 1,3-diynes

Symmetrical 1,3-diyne compounds can be easily synthesized via a transition-metal-free homocoupling reaction of 1-haloalkynes without base and oxidant. The method shows excellent functional group compatibility and high yields.