21020-31-5

Upstream product

• 66444-09-5 (2,2-Dibromo-3,3-dimethyl-cyclopropyl)-benzene 
• 917-54-4 methyllithium 
• 1111-97-3 3-chloro-3-methylbut-1-yne 
• 28557-00-8 phenylzinc chloride 
• 591-50-4 iodobenzene 
• 598-25-4 Dimethylallene 
• 6214-31-9 3-bromo-3-methylbut-1-yne 
• 1604-29-1 1,1-dimethyl-2-propynyl acetate 
• 591-51-5 phenyllithium 
• 6214-32-0 1-bromo-3-methylbuta-1,2-diene 
• 841-76-9 triphenylaluminium 
• 1612-03-9 3-methyl-1-phenyl-but-1-yne 
• 536-74-3 phenylacetylene 
• 183270-57-7 2-Methyl-2-phenylethynyl-[1,3]dithiolane 

Downstream Products

• 55845-23-3 1,1,4,4-Tetrachloro-2,2-dimethyl-5-phenyl-spiro[2.2]pentane 
• 85914-21-2 3,3-dichloro-2,2-dimethyl-1-benzylidenecyclopropane 
• 57354-78-6 1-hydroxy-3-methyl-1-phenylbut-3-en-2-one 
• 100-52-7 benzaldehyde 
• 90-02-8 salicylaldehyde 
• 7332-95-8 3-methyl-1-phenylbutane-1,2-dione 
• 21919-51-7 3-methyl-1-phenyl-buta-1,3-diene 
• 1612-03-9 3-methyl-1-phenyl-but-1-yne 
• 83605-31-6 1-methoxy-3-methyl-1-phenyl-2-butene 
• 100103-33-1 (E)-(3-methoxy-3-methylbut-1-en-1-yl)benzene 
• 106621-03-8 1-phenyl-2-dimethyl(phenyl)silyl-3-methylbut-2-ene 
• 1173936-74-7 6-methyl-1-(methylthio)-4-phenylhept-5-en-3-one 
• 1204570-85-3 C₁₈H₁₅IO₂ 
• 1204570-83-1 C₁₉H₁₈O₃ 

Relevant academic research and scientific papers

PALLADIUM(0)-PROMOTED CROSS-COUPLING OF ALLENYLMETAL COMPOUNDS WITH ARYL AND VINYL IODIDES. A NOVEL ROUTE TO ARYL- AND VINYL-SUBSTITUTED ALLENES

The reaction of allenylmetal compounds, RR'C=CHM (I), with aryl and vinyl iodides, R''I, have been studied.With Pd(PPh3)4 as catalyst a highly regioselective formation of allenes, RR'C=C=CHR'' (II), has been observed for M=MgCl, Cu, Cu1/2Li1/2, Ag, Ag1/2L

Regioselective Rh-Catalyzed Hydroformylation of 1,1,3-Trisubstituted Allenes Using BisDiazaPhos Ligand

The efficient hydroformylation of 1,1,3-trisubstituted allenes is accomplished with low loadings of a Rh catalyst supported by a BisDiazaPhos (BDP) ligand. The ligand identity is key to achieving high regioselectivity, while the mild reaction conditions m

Direct C(sp2)-C(sp3) cross-coupling of diaryl zinc reagents with benzylic, primary, secondary, and tertiary alkyl halides

The direct C(sp2)-C(sp3) cross-coupling of diaryl zinc reagents with benzylic, primary, secondary, and tertiary alkyl halides proceeded in the absence of coordinating ethereal solvents at ambient temperature without the addition of a catalyst. The C(sp2)-C(sp3) cross-coupling showed excellent functional-group tolerance, and products were isolated in high yields, generally without the requirement for purification by chromatography. This process represents an expedient, operationally simple method for the construction of new C(sp2)-C(sp3) bonds. Zinc and you'll miss it. Direct C(sp2)-C(sp3) cross-coupling of diaryl zinc reagents with alkyl halides proceeded rapidly at ambient temperature without a coordinating ethereal solvent or an added catalyst (see scheme). This versatile, operationally simple approach to C(sp2)-C(sp3) bond formation enables the expedient construction of a diverse array of carbon-based structural motifs.

Gold-catalyzed isomerization of unactivated allenes into 1,3-dienes under ambient conditions

We have developed a gold-catalyzed isomerization of unactivated allenes into 1,3-dienes with nitrosobenzene as an additive. This reaction proceeded almost exclusively at room temperature for highly substituted allenes. The utility of this reaction is manifested by the development of one-pot [4+2]-cycloaddition of allenes and reactive alkenes.

Generation of allenic/propargylic zirconium complexes and subsequent cross-coupling reactions: A facile synthesis of multisubstituted allenes

(Chemical Equation Presented) The β-alkoxide elimination reaction of propargylic ether with Negishi reagent leads to allenes and/or alkynes after hydrolysis. The product distribution is highly dependent on the substitution pattern of starting propargylic

Umpolung of carbon-sulfur bonds. Novel synthesis of substituted allenes from propargylic dithioacetals

Umpolung of the carbon-sulfur bonds can be achieved by treatment of propargylic dithioacetals 1 with organocuprates. The organocopper intermediates 3 gave the corresponding allenyl thioethers 4 upon protonolysis. When alkyl halides were used, propargylic thioethers 5 were obtained exclusively. Transmetalation of organocopper intermediates 3 with ZnBr2 followed by Pd(PPh3)4-catalyzed coupling with vinylic or aryl halides afforded the corresponding allenyl thioethers 4. Either 4 or 5 reacted with Grignard reagents in the presence of NiCl2(dppf) to yield the corresponding allenes 9 or 10, respectively. The overall reaction can be considered to use 1 as allene-1,3-zwitterion synthons. The relative reactivities of a propargylic ether versus a propargylic dithioacetal toward an organocopper reagent were compared. The sulfur moiety apparently has higher reactivity toward the copper reagent.

Integrated Chemical Process: One-Pot Double Elimination Method for Acetylenes

A novel one-pot process for synthesis of acetylenes has been achieved in which the following series of steps are integrated: addition of an α-anion of sulfone to aldehyde; trapping of the resulting adduct to incorporate a leaving group, and double elimination of this intermediate. Consolidation of Peterson elimination renders the process much simpler. This method provides a convenient and high-yielding access to a variety of enynes and polyynes as well as to functionally substituted aryl acetylenes containing halogen(s) or acetal groups, which are useful building blocks for aryl acetylene scaffolds. Iteration of the one-pot generation of acetylenic bonds provides a new metodology for the buildup of aryl acetylene skeletons.

Integrated chemical process. One-pot preparation of acetylenes by Peterson-sulfone elimination

Integration of silylation of α-sulfonyl carbanion, addition of the anion of the resulting α-silyl sulfone to aldehyde, Peterson elimination, and sulfone elimination leads to one-pot synthesis of acetylenes.

THE SILYL-CUPRATION AND STANNYL-CUPRATION OF ALLENES

The stoichiometric silyl-cupration of allene 7, followed directly by treating the intermediate cuprate with a proton, with a range of carbon electrophiles, and with chlorine gives the vinylsilanes 8-13.Alternatively, when iodine is the electrophile, the product is the vinyl iodide 16.This can then be metallated and treated with a proton or a range of carbon electrophiles to give the allylsilanes 18-21.More-substituted allenes also undergo silyl-cupration followed by protonation, phenylallenes giving vinylsilanes, and alkylallenes giving, on the whole, allylsilanes.Stoichiometric stannyl-cupration of allenes takes place, with similar but less reliable regiocontrol to that of the corresponding silyl-cupration.