cheminform abstract: aerobic, cu-catalyzed desulfitative c—c bond-forming reaction of ketene...

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ChemInform 2011, 42, issue 47 © 2011 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim Thioethers Q 0580 DOI: 10.1002/chin.201147072 Aerobic, Cu-Catalyzed Desulfitative C—C Bond-Forming Reaction of Ketene Di- thioacetals/Vinylogous Thioesters and Arylboronic Acids. — The synthesis of compounds (III), (VI), and (VIII) uses attractive, readily available ketene dithioacetals and involves dual catalysis of Cu for the activation of thioorganics without the use of an S-pendant. The use of alkenyl boronic acid or ketene dithioacetals, which have a cyclic 1,3-dicarbonyl unit or bearing only one electron-withdrawing group, does not lead to the desired products. Increasing the amount of the boronic acids (II) to 6 equiv. increase the yield by 10—20%. — (DONG, Y.; WANG, M.; LIU, J.; MA, W.; LIU*, Q.; Chem. Commun. (Cambridge) 47 (2011) 26, 7380-7382, http://dx.doi.org/10.1039/c1cc11382h ; Dep. Chem., Northeast Norm. Univ., Changchun 130024, Peop. Rep. China; Eng.) — C. Gebhardt 47- 072

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Page 1: ChemInform Abstract: Aerobic, Cu-Catalyzed Desulfitative C—C Bond-Forming Reaction of Ketene Dithioacetals/Vinylogous Thioesters and Arylboronic Acids

ThioethersQ 0580 DOI: 10.1002/chin.201147072

Aerobic, Cu-Catalyzed Desulfitative C—C Bond-Forming Reaction of Ketene Di-thioacetals/Vinylogous Thioesters and Arylboronic Acids. — The synthesis of compounds (III), (VI), and (VIII) uses attractive, readily available ketene dithioacetals and involves dual catalysis of Cu for the activation of thioorganics without the use of an S-pendant. The use of alkenyl boronic acid or ketene dithioacetals, which have a cyclic 1,3-dicarbonyl unit or bearing only one electron-withdrawing group, does not lead to the desired products. Increasing the amount of the boronic acids (II) to 6 equiv. increase the yield by 10—20%. — (DONG, Y.; WANG, M.; LIU, J.; MA, W.; LIU*, Q.; Chem. Commun. (Cambridge) 47 (2011) 26, 7380-7382, http://dx.doi.org/10.1039/c1cc11382h ; Dep. Chem., Northeast Norm. Univ., Changchun 130024, Peop. Rep. China; Eng.) — C. Gebhardt

47- 072

ChemInform 2011, 42, issue 47 © 2011 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim