22688-02-4

Upstream product

• 131190-45-9 [(E)-3-(4-Chloro-phenyl)-1-methoxy-allyl]-trimethyl-silane 
• 106-39-8 bromochlorobenzene 
• 637-87-6 1-Chloro-4-iodobenzene 
• 110388-16-4 (E)-tributyl(3-methoxyprop-1-en-1-yl)stannane 
• 24583-70-8 (E)-3-(p-chlorophenyl)prop-2-en-1-ol 
• 74-88-4 methyl iodide 
• 627-41-8 propargyl alcohol methyl ether 
• 22554-01-4 trans-3-Ethoxycarbonylamino-1-(4-chlorphenyl)-propen 
• 124-41-4 sodium methylate 

Downstream Products

• 1291104-95-4 acetic acid (1R,2S)-2-acetoxy-3-methoxy-1-(4-chlorophenyl)propyl ester 
• 1291104-90-9 acetic acid (1S,2S)-2-acetoxy-3-methoxy-1-(4-chlorophenyl)propyl ester 
• 1309474-19-8 (+)-(S)-1-chloro-4-(hept-1-en-3-yl)benzene 

Relevant academic research and scientific papers

The first example of hydrozirconation of alkynes in room temperature ionic liquids

Hydrozirconation of terminal alkynes in 1-butyl-3-methylimidazolium hexafluorophosphate ([bmim][PF6]) at 30 °C gave highly regio- and stereoselectively (E)-vinylzirconium complexes, which underwent a cross-coupling reaction with aryl halides in the presence of Pd(PPh 3)4 to afford (E)-1,2-disubstituted ethenes in good to high yields. Our system not only avoids the use of easily volatile THF or CH2Cl2 as solvent but also solves the basic problem of palladium catalyst reuse.

Enantioselective Prevost and Woodward reactions using chiral hypervalent iodine(iii): Switchover of stereochemical course of an optically active 1,3-dioxolan-2-yl cation

Optically active 1,3-dioxolan-2-yl cation intermediates were generated during enantioselective dioxyacetylation of alkene with chiral hypervalent iodine(III). Regioselective attack of a nucleophile toward the intermediate resulted in reversal of enantioselectivity of the dioxyacetylation. The Royal Society of Chemistry.

MCM-41-supported bidentate phosphine palladium(0) complex as an efficient catalyst for the heterogeneous Stille reaction

A Stille coupling reaction of organostannanes with organic halides has been developed in the presence of a catalytic amount of MCM-41-supported bidentate phosphine palladium(0) complex (0.5 mol %) in DMF/H2O (9:1) under air atmosphere in high yields. This polymeric palladium catalyst exhibits higher activity than Pd(PPh3)4 and can be reused at least 10 times without any decrease in activity.

ORGANOTIN HOMOENOLATE EQUIVALENTS - ACCESS TO β-ACYL- AND β-ARYL-PROPIONALDEHYDES THROUGH HETEROSUBSTITUTED ALLYLTINS AND VINYLTINS

Although, α-ethoxycrotyltributyltin can be used as an equivalent of the homoenolate anion CH3-CHCH2CHO in reactions with acyl chlorides, the non-substituted α-ethoxyallyltributyltin could not be employed in this way. γ-Methoxyvinyltins, easily prepared by hydrostannation of propargylic ethers, are successfully employed as synthetic equivalents of the homoenolate anions -CH2CH2CHO and -CH2CH2COCH3 in reactions with acyl chlorides.A silylated γ-methoxyvinyltin, which is both a vinyltin and an allylsilane, reacts with acyl chlorides and aryl bromides as a promising equivalent of the homoenolate anion -CH2CH2CHO and tolerates a wide range of other reactive functional groups.

An easy access to β-acyl- and β-aryl-propionaldehydes through a new silylated organotin homoenolate equivalent

Palladium-catalysed cross-coupling of a new umpolung reagent, (α-methoxy-γ-tributylstannyl)allyltrimethyl-silane, with acyl or aryl halides, involves exclusively the vinyl-tin bond and subsequent desilylation with tetrabutylammonium fluoride gives enol ethers, precursors of β-acyl- or β-aryl-propionaldehydes.