79644-41-0

Upstream product

• 75-89-8 2,2,2-trifluoroethanol 
• 93362-63-1 (1E,3Z)-1,4-dimethylhepta-1,3-diene-5-ynyl trifluoromethanesulphonate 
• 358-23-6 trifluoromethylsulfonic anhydride 
• 2416-94-6 2,3,6-trimethylphenol 

Downstream Products

• 58720-40-4 4-(2,3,6-trimethyl-phenyl)-butan-2-one 
• 57461-21-9 (3E)-4-(2,3,6-trimethylphenyl)but-3-en-2-one 

Relevant academic research and scientific papers

INHIBITING HUMAN INTEGRIN α4β7

Disclosed are small molecule antagonists of human α4β7 integrin, and methods of using them to treat a number of diseases and conditions.

Transition-Metal-Free C-C, C-O, and C-N Cross-Couplings Enabled by Light

Transition-metal-catalyzed cross-couplings to construct C-C, C-O, and C-N bonds have revolutionized chemical science. Despite great achievements, these metal catalysts also raise certain issues including their high cost, requirement of specialized ligands, sensitivity to air and moisture, and so-called "transition-metal-residue issue". Complementary strategy, which does not rely on the well-established oxidative addition, transmetalation, and reductive elimination mechanistic paradigm, would potentially eliminate all of these metal-related issues. Herein, we show that aryl triflates can be coupled with potassium aryl trifluoroborates, aliphatic alcohols, and nitriles without the assistance of metal catalysts empowered by photoenergy. Control experiments reveal that among all common aryl electrophiles only aryl triflates are competent in these couplings whereas aryl iodides and bromides cannot serve as the coupling partners. DFT calculation reveals that once converted to the aryl radical cation, aryl triflate would be more favorable to ipso substitution. Fluorescence spectroscopy and cyclic voltammetry investigations suggest that the interaction between excited acetone and aryl triflate is essential to these couplings. The results in this report are anticipated to provide new opportunities to perform cross-couplings.

Phenyl Cations as Reactive Intermediates in the Solvolysis of Dien-in-yl Triflates

The synthesis, separation, and solvolysis of the stereoisomeric 1,4-dimethyl-1,3-hexadien-5-yn-1-yl triflates 15a - c in various solvents are described.In contrast to the (Z)-isomers 15a - c, the (E)-isomers 15a - c react preferably via an intermediate phenyl cation 16 to give the phenyl ethers 17.Further mechanistic investigations which support the formation of the intermediate phenyl cations 16 are described.The formation of the benzylic derivatives 18 is discussed.

Experimental Evidence for a Phenyl Cation Intermediate in the Solvolysis Reactions of Dienynyl Trifluoromethanesulphonates

The synthesis, separation, and solvolysis of the stereoisomeric dienynyl trifluoromethanesulphonates (1) are described, whereby the E-isomers, in contrast with the Z-isomers, rearrange to a remarkable extent to form the phenyl ethers (5) via the phenyl cations (2).