205108-16-3

Upstream product

• 229015-31-0 (+/-)-4-[4-(trifluoromethyl)phenyl]but-3-yn-2-ol 
• 455-19-6 4-Trifluoromethylbenzaldehyde 
• 1607843-36-6 C₁₅H₁₆F₃N 
• 128796-39-4 4-trifluoromethylphenylboronic acid 

Downstream Products

• 205108-18-5 (E)-1-(buta-1,3-dien-1-yl)-4-(trifluoromethyl)benzene 
• 57132-18-0 (E)-4-(4-(trifluoromethyl)phenyl)-3-buten-2-ol 
• 1607843-53-7 (E)-2,2,6,6-tetramethyl-1-((3-phenyl-4-(4-(trifluoromethyl)phenyl)but-3-en-2-yl)oxy)piperidine 
• 1607843-71-9 C₂₆H₃₂F₃NO 
• 1380423-65-3 (E)-benzyl 4-(4-(trifluoromethyl)phenyl)but-3-en-2-ylcarbamate 

Relevant academic research and scientific papers

Kinetics and Mechanism of Allene Racemization Catalyzed by a Gold N-Heterocyclic Carbene Complex

The kinetics of the racemization of 1,3-disubstituted allenes catalyzed by (IPr)AuOTf (IPr = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidine) has been investigated. The rate of gold-catalyzed allene racemization obeyed the following second-order rate law: rate = krac[allene][Au]. An analysis of the rate of the gold-catalyzed racemization of 1-aryl-1,2-butadienes as a function of allene electron donor ability established moderate depletion of electron density on the C1 allenyl carbon atom in the rate-limiting transition state for racemization. Analysis of the temperature dependence of the rate of racemization of 1-(p-tolyl)-1,2-butadiene established the activation parameters ΔH∞ = 8.3 ± 1 kcal mol-1 and ΔS∞ = -28 ± 4 eu. These observations were in accord with a mechanism for allene racemization involving turnover-limiting, intermolecular allene exchange followed by rapid allene stereomutation.

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.

Copper-catalyzed regio- and stereoselective intermolecular three-component oxyarylation of allenes

A copper(II)-catalyzed intermolecular three-component oxyarylation of allenes using arylboronic acids as a carbon source and TEMPO as an oxygen source is described. The reaction proceeded under mild conditions with high regio- and stereoselectivity and functional group tolerance. A plausible reaction mechanism is proposed, involving carbocupration of allenes, homolysis of the intervening allylcopper(II), and a radical TEMPO trap.

Gold(I)-catalyzed hydration of allenes

A gold(I) N-heterocyclic carbene complex catalyzes the intermolecular hydration of allenes to form allylic alcohols in modest yield with selective delivery of water to the terminal carbon atoms of the allenyl moiety.