32644-22-7

Upstream product

• 408320-58-1 (1,2,2,3-tetrachloro-butyl)-benzene 
• 16169-88-3 1-phenylprop-2-ynyl acetate 
• 594-02-5 1,1-diiodoethane 
• 536-74-3 phenylacetylene 
• 591-50-4 iodobenzene 
• 53487-52-8 1-methylprop-2-ynyl p-toluenesulfonate 
• 10575-78-7 1-brombuta-1,2-diene 
• 28557-00-8 phenylzinc chloride 
• 75-16-1 methylmagnesium bromide 
• 27975-80-0 (+/-)-3-bromo-1-phenyl-1-butyne 
• 29333-27-5 but-3-yn-2-yl benzoate 
• 3958-47-2 triphenylindium 
• 2327-98-2 (R)-buta-1,2-dien-1-ylbenzene 
• 73922-81-3 4-phenyl-but-3-yn-2-ol 

Downstream Products

• 85914-22-3 2-methyl-3-phenyl-1-(dichloromethylene)cyclopropane 
• 85914-09-6 3,3-dichloro-2-methyl-1-benzylidenecyclopropane 
• 935-00-2 trans-4-phenyl-2-butene 
• 1560-09-4 (Z)-but-1-en-1-ylbenzene 
• 1005-64-7 trans-1-phenyl-1-butene 
• 104-51-8 1-butylbenzene 
• 15324-90-0 (2Z)-but-2-en-1-ylbenzene 
• 824-90-8 1-phenylbut-1-ene 
• 622-76-4 1-phenyl-1-butyne 
• 1560-06-1 1-phenyl-2-butene 
• 33598-22-0 1-Phenyl-3-methylprop-2-yne 
• 21165-36-6 1-Ethoxy-1-phenyl-2-butanone 
• 208984-11-6 dimethyl (S)-(-)-(1,2-diphenyl-1-buten-3-yl)propanedioate 
• 15854-66-7 2.3-Dichlor-1-phenyl-buten-⁽²⁾ 

Relevant academic research and scientific papers

Direct Deamination of Primary Amines via Isodiazene Intermediates

We report here a reaction that selectively deaminates primary amines and anilines under mild conditions and with remarkable functional group tolerance including a range of pharmaceutical compounds, amino acids, amino sugars, and natural products. An anomeric amide reagent is uniquely capable of facilitating the reaction through the intermediacy of an unprecedented monosubstituted isodiazene intermediate. In addition to dramatically simplifying deamination compared to existing protocols, our approach enables strategic applications of iminium and amine-directed chemistries as traceless methods. Mechanistic and computational studies support the intermedicacy of a primary isodiazene which exhibits an unexpected divergence from previously studied secondary isodiazenes, leading to cage-escaping, free radical species that engage in a chain, hydrogen-atom transfer process involving aliphatic and diazenyl radical intermediates.

Intermolecular Allene Functionalization by Silver-Nitrene Catalysis

Under silver catalysis conditions, using [Tp*,BrAg]2 as the catalyst precursor, allenes react with PhI═NTs in the first example of efficient metal-mediated intermolecular nitrene transfer to such substrates. The nature of the substituent at the allene seems crucial for the reaction outcome since arylallenes are converted into azetidine derivatives, whereas methylene aziridines are the products resulting from alkylallenes. Mechanistic studies allow proposing that azetidines are formed through unstable cyclopropylimine intermediates, which further incorporate a second nitrene group, both processes being silver-mediated. Methylene aziridines from alkylallenes derive from catalytic nitrene addition to the allene double bonds. Both routes have resulted to be productive for further synthetic transformations affording aminocyclopropanes.

Stereoselective annulation between an allene, an alkene, and two nitrosoarenes to access bis(isoxazoliodine) derivatives

This work reports metal-free annulations between one allene, two nitrosoarenes and one electron-deficient alkene to afford bis(isoxazolidine) derivatives stereoselectively. This process involves an initial formation of isoxazolidin-4-imine oxides, followe

Enantioselective, Stereodivergent Hydroazidation and Hydroamination of Allenes Catalyzed by Acyclic Diaminocarbene (ADC) Gold(I) Complexes

The gold-catalyzed enantioselective hydroazidation and hydroamination reactions of allenes are presented herein. ADC gold(I) catalysts derived from BINAM were critical for achieving high levels of enantioselectivity in both transformations. The sense of enantioinduction is reversed for the two different nucleophiles, allowing access to both enantiomers of the corresponding allylic amines using the same catalyst enantiomer. Chiral allylic azides and amines are obtained by enantioselective hydroazidation and hydroamination of allenes catalyzed by acyclic diaminocarbene gold(I) catalysts derived from BINAM. The sense of enantioinduction is reversed for the two different nucleophiles, allowing easy access to both enantiomers with a single catalyst enantiomer.

Organomagnesium-catalyzed isomerization of terminal alkynes to allenes and internal alkynes

Organomagnesium complexes 2 were synthesized from N,N-dialkylamineimine ligands 1 and dibenzylmagnesium by benzylation of the imine moiety. 3-Aryl-1-propynes reacted with 2 to form the corresponding tetraalkynyl complexes, which acted as catalysts for the transformation of these terminal alkynes into allenes and further to internal alkynes under mild conditions. To the best of our knowledge, this example is the first of an organomagnesium-catalyzed isomerization of alkynes. Notably, the reactions proceeded through temporally separated autotandem catalysis, thus allowing the isolation of the allene or internal alkyne species in good yields. Mechanistic experiments suggested that the catalytically active tetraalkynyl complexes consist of a tautomeric mixture of alkynyl-, allenyl-, and propargylmagnesium species.

Nickel-catalyzed substitution reactions of propargyl halides with organotitanium reagents

A simple and mild catalytic coupling reaction of propargyl halides with organotitanium reagents is reported. The reaction of propargyl bromide with organo-titanium reagents mediated by NiCl2(2 mol%) and PCy3(4 mol%) in CH2

Gold-catalyzed hydrofunctionalization of allenes with nitrogen and oxygen nucleophiles and its mechanistic insight

A wide range of nucleophiles, such as amines and alcohols, reacted intermolecularly with various allenes in the presence of gold catalysts to give the corresponding hydrofunctionalization products in high yields. The intermolecular hydroamination of chira

1,3-Li/H shift of 1-Aryl-1,2-alkadienyl reagents: An experimental and theoretical study

A mechanism involving the exchange of equilibrated protons initiated by a catalytic amount of a proton donor, the most effective of which appears to be di-isopropylamine was proposed. The thermodynamic potential of the rearrangement was first examined com

Regio- And stereoselective synthesis of alkyl allylic ethers via gold(l)-catalyzed intermodular hydroalkoxylation of allenes with alcohols

Reaction of 1-phenyl-1,2-butadiene with 2-phenyl-1-ethanol catalyzed by a 1:1 mixture of a gold(l) W-heterocyclic carbene complex and AgOTf at room temperature for 1 h led to isolation of (E)-(3-phenethoxy-1-butenyl)benzene in 96% yield as a single regio-

Gold-catalyzed intermolecular hydroalkoxylation of allenes; difference in mechanism between hydroalkoxylation and hydroamination

A wide range of alcohols 2 react with various allenes 1 in the presence of ClAuPPh3/AgOTf catalyst at ambient temperature without solvent to produce allylic ethers 3. Contrary to the hydroamination, which proceeds through high chiral-face selec