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Volumn 72, Issue 12, 2007, Pages 4440-4448

Palladium(0)-catalyzed, copper(I)-mediated coupling of boronic acids with cyclic thioamides. Selective carbon-carbon bond formation for the functionalization of heterocycles

Author keywords

[No Author keywords available]

Indexed keywords

AROMATICITY; BORONIC ACIDS; CROSS-COUPLING PROTOCOL; CYCLIC THIOAMIDES; HETEROCYCLIC STRUCTURES;

EID: 34250202514     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo070408f     Document Type: Article
Times cited : (121)

References (81)
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    • For relevant reviews in this field, see: a, de Meijere, A, Diederich, F, Eds, Wiley-VCH: Weinheim, Germany
    • For relevant reviews in this field, see: (a) Miyaura, N. In Metal-Catalyzed Cross-Coupling Reactions; de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, Germany, 2004; Vol. 1, p 41.
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    • See also ref 4
    • (c) See also ref 4.
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    • For Cu-mediated C-S cross couplings of a cyclic thioamide with boronic acids, see: a
    • For Cu-mediated C-S cross couplings of a cyclic thioamide with boronic acids, see: (a) Bakkestuen, A. K.; Gundersen, L.-L. Tetrahedron Lett. 2003, 44, 3359.
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    • Bakkestuen, A.K.1    Gundersen, L.-L.2
  • 39
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    • For recent examples of Pd-catalyzed C-S cross-couplings involving aryl and alkyl thiols with aryl halides, see: (a) Li, G. Y, Zheng, G, Noonan, A. F. J. Org. Chem. 2001, 66, 8677
    • For recent examples of Pd-catalyzed C-S cross-couplings involving aryl and alkyl thiols with aryl halides, see: (a) Li, G. Y.; Zheng, G.; Noonan, A. F. J. Org. Chem. 2001, 66, 8677.
  • 43
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    • For recent examples of Cu-mediated C-S cross-coupling of aryl and alkyl thiols with arylhalides, see: a
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  • 47
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    • To the best of our knowledge, the only example of desulfitative carbon-carbon cross couplings of organosulfur compounds containing thiol groups involves Ni-catalyzed Kumada-type couplings of thiophenols with Grignard reagents: Wenkert, E.; Ferreira, T. W.; Michelotti, E. L. J. Chem. Soc., Chem. Commun. 1979, 637.
    • To the best of our knowledge, the only example of desulfitative carbon-carbon cross couplings of organosulfur compounds containing thiol groups involves Ni-catalyzed Kumada-type couplings of thiophenols with Grignard reagents: Wenkert, E.; Ferreira, T. W.; Michelotti, E. L. J. Chem. Soc., Chem. Commun. 1979, 637.
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    • Hosseini, M.1    Stiasni, N.2    Barbieri, V.3    Kappe, C.O.4
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    • An equimolar mixture of thioamide 1c and CuTC in dry and degassed THF rapidly forms an insoluble Cu-complex that after isolation can be used as a starting material for the reaction with phenylboronic acid in the presence of catalytic amounts of Pd(PPh3)4 to produce the desired carbon-carbon cross coupling product. For the formation and structures of various multinuclear Cu(I)-thioamide complexes, see: (a) Wycliff, C, Bharathi, D. S, Samuelson, A. G, Nethaji, M. Polyhedron 1999, 18, 949
    • 4 to produce the desired carbon-carbon cross coupling product. For the formation and structures of various multinuclear Cu(I)-thioamide complexes, see: (a) Wycliff, C.; Bharathi, D. S.; Samuelson, A. G.; Nethaji, M. Polyhedron 1999, 18, 949.


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