21368-69-4Relevant academic research and scientific papers
Enantioselective Heck Arylation of Acyclic Alkenol Aryl Ethers: Synthetic Applications and DFT Investigation of the Stereoselectivity
Polo, Ellen Christine,Wang, Martí Fernández,Angnes, Ricardo Almir,Braga, Ataualpa A. C.,Correia, Carlos Roque Duarte
supporting information, p. 884 - 892 (2019/12/30)
Herein we report the enantioselective Heck-Matsuda arylation of acyclic E and Z-alkenyl aryl ethers. The reactions were carried out under mild conditions affording the enantioenriched benzyl ethers in a regioselective manner, moderate to good yields (up to 73%), and in good to excellent enantiomeric ratios (up to 97:3). The enantioselective Heck-Matsuda arylation has shown a broad scope (25 examples), and some key Heck-Matsuda adducts were further converted into more complex and valuable scaffolds including their synthetic application in the synthesis of (R)-Fluoxetine, (R)-Atomoxetine, and in the synthesis of an enantioenriched benzo[c]chromene. Finally, in silico mechanistic investigations into the reaction's enantioselectivity were performed using density functional theory. (Figure presented.).
Metal-free oxidative cyclization of alkynyl aryl ethers to benzofuranones
Graf, Katharina,Ruehl, Carmen L.,Rudolph, Matthias,Rominger, Frank,Hashmi, A. Stephen K.
supporting information, p. 12727 - 12731 (2013/12/04)
Readily available phenols can be converted into substituted aryl alkynyl ethers, which react with an N-oxide as an oxidant and catalytic amounts of a Bronsted acid to provide benzofuranones. If non-terminal alkynyl ethers are applied, a 1,2-hydride shift takes place and phenyl acrylates are obtained. Thus activated alkynes can serve as α-oxy carbene precursors even in the absence of a metal catalyst. Copyright
Rhodium-catalyzed complete regioselective lntermolecular cross-cyclotrimerization of aryl ethynyl ethers and nitriles or isocyanates at room temperature
Komine, Yoshiyuki,Tanaka, Ken
supporting information; experimental part, p. 1312 - 1315 (2010/06/15)
Chemical Equation Presented We have established that a catlonic rhodium(I)/H8- BINAP complex catalyzes the complete regioselective intermolecular cross-cyclotrimerizatlon of aryl ethynyl ethers and nitriles or isocyanates leading to 2,4-diaryloxypyrldines or 4,6-diaryloxy-2-pyridones at room temperature.
