3972-22-3Relevant articles and documents
Ni-Catalyzed Borylation of Aryl Sulfoxides
Huang, Mingming,Wu, Zhu,Krebs, Johannes,Friedrich, Alexandra,Luo, Xiaoling,Westcott, Stephen A.,Radius, Udo,Marder, Todd B.
supporting information, p. 8149 - 8158 (2021/05/10)
A nickel/N-heterocyclic carbene (NHC) catalytic system has been developed for the borylation of aryl sulfoxides with B2(neop)2 (neop=neopentyl glycolato). A wide range of aryl sulfoxides with different electronic and steric properties were converted into the corresponding arylboronic esters in good yields. The regioselective borylation of unsymmetric diaryl sulfoxides was also feasible leading to borylation of the sterically less encumbered aryl substituent. Competition experiments demonstrated that an electron-deficient aryl moiety reacts preferentially. The origin of the selectivity in the Ni-catalyzed borylation of electronically biased unsymmetrical diaryl sulfoxide lies in the oxidative addition step of the catalytic cycle, as oxidative addition of methoxyphenyl 4-(trifluoromethyl)phenyl sulfoxide to the Ni(0) complex occurs selectively to give the structurally characterized complex trans-[Ni(ICy)2(4-CF3-C6H4){(SO)-4-MeO-C6H4}] 4. For complex 5, the isomer trans-[Ni(ICy)2(C6H5)(OSC6H5)] 5-I was structurally characterized in which the phenyl sulfinyl ligand is bound via the oxygen atom to nickel. In solution, the complex trans-[Ni(ICy)2(C6H5)(OSC6H5)] 5-I is in equilibrium with the S-bonded isomer trans-[Ni(ICy)2(C6H5)(SOC6H5)] 5, as shown by NMR spectroscopy. DFT calculations reveal that these isomers are separated by a mere 0.3 kJ/mol (M06/def2-TZVP-level of theory) and connected via a transition state trans-[Ni(ICy)2(C6H5)(η2-{SO}-C6H5)], which lies only 10.8 kcal/mol above 5.
A simple one-pot and transition metal-free synthesis of diaryl- and dialkyl sulfides via grignard reaction/deoxygenation
Jung, Hee Seon,Suh, Nuri,Jeon, Heung Bae
supporting information, p. 779 - 782 (2016/05/19)
-
Polystyrene and silica gel-supported, AlCl3-catalyzed preparation of diaryl sulfoxides from arenes and thionyl chloride
Boroujeni, Kaveh Parvanak
experimental part, p. 2085 - 2091 (2010/12/19)
A simple, chemoselective, and efficient method has been developed for direct conversion of arenes to symmetrical diaryl sulfoxides using thionyl chloride in the presence of a catalytic amount of cross-linked polystyrene-supported aluminium chloride (Ps-AlCl3) and silica gel-supported aluminium chloride (SiO2-AlCl3). These solid acid catalysts are stable and can be easily recovered and reused without appreciable change in their efficiency. Copyright Taylor & Francis Group, LLC.