27975-80-0

Upstream product

• 73922-81-3 4-phenyl-but-3-yn-2-ol 
• 76651-94-0 4-phenylbut-3-yn-2-yl methanesulfonate 
• 591-50-4 iodobenzene 
• 100-42-5 styrene 
• 102921-26-6 (1,2-dibromoethyl)benzene 
• 536-74-3 phenylacetylene 

Downstream Products

• 54857-14-6 1-(2,4-Dimethyl-6-phenyl-hex-1-en-5-yne-3-sulfonyl)-4-methyl-benzene 
• 92654-71-2 3,4-Dimethyl-1-phenylheptin-⁽¹⁾-ol-⁽⁴⁾ 
• 4254-27-7 3-Ethylmercapto-1-phenyl-but-1-in 
• 21223-33-6 (1-methyl-3-phenyl-prop-2-ynyl)-boronic acid dibutyl ester 
• 57354-90-2 5-methyl-3-phenyl-4-nitroisoxazole 
• 73922-81-3 4-phenyl-but-3-yn-2-ol 
• 622-76-4 1-phenyl-1-butyne 
• 32644-22-7 1-methyl-3-phenylallene 
• 71313-53-6 2-Methyl-dodeca-1,3,4-trien 
• 2327-98-2 (+)-1-Phenylbuta-1,2-dien 
• 75079-84-4 4-nitro-3-methyl-5-phenylisoxazole 
• 77305-92-1 C₁₀H₉⁽¹⁺⁾ 
• 30979-50-1 3-Methyl-1,1-diphenyl-1,2-butadiene 
• 17066-24-9 2-Methyl-4-phenyl-3-butynoylchlorid 

Relevant academic research and scientific papers

Regioselective Iron-Catalysed Cross-Coupling Reaction of Aryl Propargylic Bromides and Aryl Grignard Reagents

An iron-catalysed Kumada-type cross-coupling reaction between aryl substituted propargylic bromides and arylmagnesium reagents has been developed. Propargylic coupling products were the main or only outcome, and propargyl/allene regioselectivity was shown to depend on the electronic nature of the substituents on the triple bond of the substrate and on the arylmagnesium halide. Best selectivities were observed when electron donating substituents were present in either reagent. The process is stereoespecific, occurs with configuration inversion and no carbon-based radicals seem to be involved in the mechanism. (Figure presented.).

Synthesis of Spirobicyclic Pyrazoles by Intramolecular Dipolar Cycloadditions/[1s, 5s] Sigmatropic Rearrangements

The formation of fused pyrazoles via intramolecular 1,3-dipolar cycloadditions of diazo intermediates with pendant alkynes is described. A subsequent thermal [1s, 5s] sigmatropic shift of these pyrazole systems resulted in a ring contraction, forming spirocyclic pyrazoles. The limitations of this rearrangement were explored by changing the substituents on the nonmigrating aromatic ring and by using substrates lacking an aromatic linkage to the propargyl group.

Iron-Catalyzed Coupling of Propargyl Bromides and Alkyl Grignard Reagents

An iron-catalyzed Kumada-type cross-coupling reaction of propargyl halides with alkylmagnesium reagents is described. The reaction is fast, takes place in smooth conditions, tolerates several functional groups that would be able to react with the Grignard reagent, and may afford either allene or propargyl coupling derivatives. Factors involved in the observed regioselectivity have been studied.

NiICatalyzes the Regioselective Cross-Coupling of Alkylzinc Halides and Propargyl Bromides to Allenes

We describe the unprecedented formation of allenes by Ni-catalyzed cross-coupling of propargyl bromides with alkylzinc halides. The reaction regioselectivity is complementary to the previously reported formation of propargyl-coupled compounds. Experiments

Lactone radical cyclizations and cyclization cascades mediated by SmI 2-H2O

Unsaturated lactones undergo reductive radical cyclizations upon treatment with SmI2-H2O to give decorated cycloheptanes in a single highly selective operation during which up to three contiguous stereocenters are generated. Furthermore, cascade processes involving lactones bearing two alkenes, an alkene and an alkyne, or an allene and an alkene allow "one-pot" access to biologically significant molecular scaffolds with the construction of up to four contiguous stereocenters. The cyclizations proceed by the trapping of radical anions formed by electron transfer reduction of the lactone carbonyl.

Iodocyclization of hydroxylamine derivatives based on the control of oxidative aromatization leading to 2,5-dihydroisoxazoles and isoxazoles

An efficient method for the synthesis of 2,5-dihydroisoxazoles and isoxazoles using iodocyclization of N-alkoxycarbonyl O-propargylic hydroxylamines has been developed. 2,5-Dihydro-4-iodoisoxazole underwent the cross-coupling reactions without aromatization to afford polyfunctionalized 2,5-dihydroisoxazoles. This process was applied to the preparation of valdecoxib and its 2,5-dihydro-derivative.

Rhodium(l)-catalyzed carbonyl allenylation versus propargylation via redox transmetalation across tetragonal tin(ll) oxide

A reagent combination of β-SnO and catalytic [Rh(COD)Cl]2 in THF-H2O promotes the reaction of propargyl bromides and aldehydes and directs the regioselectivity toward the formation of either allenic alcohols or homopropargylic alcohols. This highly regioselective either/or transformation proceeds via a transmetalation from rhodium to tin, in which metallotropic rearrangement between a propargylmetal and allenylmetal is arrested.

CHIRAL RECOGNITION OF ALLENIC HYDROCARBONS BY 1H NMR

The syntheses of the allenes (+/-)-1, (+/-)-4, and (+/-)-6 as well as of the enriched samples (-)-1, (-)-4 and (-)-6 are described. 1H NMR shifts and splittings induced by a mixture of the achiral salt Ag(fod) and the optically active complex (+)-Yb(hfbc)

Choix des methodes pour la synthese univoque de carbures acetyleniques. Troisieme partie : Arylacetylenes et aryl-1 alcynes-1

The range of applicability of six syntheses of pure alkynes with one aryl group has been defined; a short review of other possible procedures is included.We have specified the best method to obtain selectively the alkynes Ar-CCH and Ar-CC-R, according to the nature of the substituents of the aryl group and according to the developed structure of the R group.It is thus possible to recommend with the largest probability of success the method to obtain, in homogenous series, alkynes corresponding to still more complicated structures.