160254-75-1

Upstream product

• 591-50-4 iodobenzene 
• 629-05-0 n-octyne 
• 201230-82-2 carbon monoxide 
• 2528-61-2 Heptanoic acid chloride 
• 32584-71-7 diphenyl(phenylethynyl)stibine 
• 536-74-3 phenylacetylene 
• 28995-82-6 ((Z)-1-Iodo-2-methanesulfonyl-vinyl)-benzene 
• 111-71-7 heptanal 
• 24378-05-0 methyl phenylethynyl sulfone 
• 3761-92-0 n-hexylmagnesium bromide 
• 2579-22-8 Phenylpropargyl aldehyde 
• 81438-46-2 1-iodooct-1-yne 
• 611-73-4 Benzoylformic acid 
• 126472-97-7 12-phenylethynyl-N-methyl-5,6,7,12-tetrahydrodibenz[c,f][1,5]azastibocine 

Downstream Products

• 1413809-77-4 tert-butyl furan-2-yl(2-hydroxy-2-(phenylethynyl)octyl)-carbamate 

Relevant academic research and scientific papers

Palladium-catalyzed cross-coupling reactions between 1-alkynylstibines and acyl chlorides

1-Alkynyldiphenylstibines react with acyl chlorides in dichloroethane in the presence of a palladium(0) or (II) catalyst to afford alkynyl ketones by cross-coupling reaction in good to moderate yields. These reactions are highly substituent-selective in that only the alkynyl group could be transferred from the antimony compounds, even in the presence of a large excess of acyl chlorides. (C) 2000 Elsevier Science Ltd.

Decatungstate as Direct Hydrogen Atom Transfer Photocatalyst for SOMOphilic Alkynylation

A versatile approach for the alkynylation of a variety of aliphatic hydrogen donors, including alkanes, is reported. We used tetrabutylammonium decatungstate as photocatalyst to generate organoradicals from C-H/Si-H bonds via hydrogen atom transfer. The l

Photocatalytic Annulation-Alkynyl Migration Strategy for Multiple Functionalization of Dual Unactivated Alkenes

A novel photoredox catalysis for multiple functionalization of two different types of unactivated alkenes in a single operation was reported through a conceptually new mode of annulation-alkynyl migration. A wide array of cyclopentane carboxylates were sy

One-pot regioselective synthesis of substituted pyrazoles and isoxazoles in PEG-400/water medium by Cu-free nano-Pd catalyzed sequential acyl Sonogashira coupling-intramolecular cyclization

Catalyst efficacy of in situ generated Pd-nanoparticles (PdNPs) in the regioselective one-pot synthesis of 3,5-di & 3,4,5-trisubstituted pyrazoles and 3,5-disubstituted isoxazoles in environmentally benign PEG-400/H2O medium, which involves the sequential (i) Cu-free acyl-Sonogashira coupling (ASC) and (ii) intramolecular ynone-amine cyclization under PTC conditions was described. The results of controlled experiments support the operation of two sequential catalytic cycles (ASC/cyclization) and achievement of complementary/opposite regioselectivity via ynone-bound palladium in a one-pot approach. Moreover, the in situ PdNPs recovered after the first catalytic cycle of the one-pot reaction sequence have been reused again five times successively. Besides, prior to the above studies, the efficacy of some common Pd-N-heterocyclic carbene (Pd-NHC) complexes in catalyzing the same one-pot two-step reaction sequence (Cu-free ASC/cyclization) both in water and organic solvents was also optimized. In situ generation of PdNPs from above Pd-NHCs in water was also identified, but they are not reusable due to their large size distribution.

A general two-step one-pot synthesis process of ynones from α-keto acids and 1-iodoalkynes

A general two-step one-pot synthesis process of ynones was developed by cycloaddition of α-keto acids and 1-iodoalkynes followed by a ring-opening reaction. Its easy conditions and novel mechanism endowed it with two distinctive advantages: iodine-atom bonded to C(sp2) remained intact and α-keto acids became a part of the triple bonds in ynones.

Pd-Catalyzed Cross-Coupling of Terminal Alkynes with Chromium(0) Fischer Carbene Complexes

Alkyl chromium(0) carbene complexes typically undergo cycloadditions with alkynes to afford carbo- or heterocyclic compounds. In the presence of Pd catalyst, it is demonstrated that a traditional cycloaddition pathway is completely altered: instead of cyc

Hypervalent organoantimony compounds 12-ethynyl-tetrahydrodibenz[c,f][1,5]azastibocines: Highly efficient new transmetallating agent for organic halides

Extremely efficient and high-speed ethynylation of acyl chlorides, aryl iodides and bromides was demonstrated by palladium-catalyzed cross-coupling reaction of N-t-butyl-Sb-ethynyl-5,6,7,12-tetrahydrodibenz[c,f][1,5]azastibocine under mild conditions. Optimization and generalization of the hypervalent antimony-mediated coupling reaction are presented in detail. Single-crystal X-ray analysis of the N-methyl-1,5-azastibocine revealed that the remarkable reactivity enhancement of the azastibocine was derived from elongation of the antimony-ethynyl carbon bond originated from Sb-N intramolecular non-bonding interaction.

Remarkable reactivity enhancement with Sb?N inter-coordination of ethynyl-1,5-azastibocines in Pd-catalyzed cross-coupling reactions with organic halides

The reaction of 12-arylethynyl-6-methyl-5,6,7,12-tetrahydrodibenzo[c,f][1, 5]-azastibocines with organic halides such as acyl halides and aryl halides in the presence of PdCl2(PPh3)2 as a catalyst led to the formation of cross-coupling products, alkynyl ketones and diaryl acetylenes, in good yields. The reactivity of the ethynyl group on the 1,5-azastibocines was far superior to that on diphenyl(phenylethynyl)stibane, which brought about marked improvement in the reaction conditions (lower temperature and shorter reaction time) and in the yields of the cross-coupling products. Single-crystal X-ray analysis of the ethynyl-1,5-azastibocine showed the presence of intramolecular Sb?N interaction which should be responsible for the remarkable reactivity enhancement of the 1,5-azastibocines for this type of reaction.

Coupling and carbonylation of iodoaromatics and terminal alkynes or alkynols catalyzed by a dimeric palladium hydroxide

The palladium(II) complex [(Ph3P)Pd(Ph)(μ-OH)]2 is an effective catalyst for the coupling aud carbonylation of alkynes and iodoarenes to give acetylenic ketones in 63-94% yields. Acetylenic hydroxy ketones were formed using secondary or tertiary alkynols as reactants.