Catalytic Heterofunctionalization 2005 by A. Togni, H. Grützmacher

By A. Togni, H. Grützmacher

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The hydroboration of thioalkynes with catecholborane in the presence of a nickel or palladium catalyst yields β-(alkylthio)-1-alkenylboronates (72a) 19 20 1 Hydroboration, Diboration, Silylboration and Stannylboration [39], and the uncatalyzed reaction of (dicyclohexyl)borane (Chx2BH) provides α(alkylthio) derivatives (72b) [41]. Since the vinylic sulfide is synthetically equivalent to a carbonyl compound, the palladium-catalyzed cross-coupling of 72a with aromatic halide having an ortho-acetylamino or a protected hydroxy group provides valuable precursors for heterocyclic compounds [86].

Int. Ed. Engl. 1998, 37, 1786-1801. (c) T. B. Marder, N. Norman, Topics in Catalysis, 1998, 5, 63-73. (d) G. J. Irvine, M. J. Lesley, T. B. Marder, N. C. Norman, C. R. Rice, E. G. Robins, W. R. Roper, G. R. Whittel, L. J. Wright, Chem. Rev. 1998, 98, 2685-2722. (e) L-B. Han, M. Tanaka, Chem. Commun. 1999, 395-402. (f) T. Ishiyama, N. Miyaura, J. Synthetic Organic Chemistry, Japan, 1999, 57, 503511. 3 Reviews for uncatalyzed hydroboration: (a) T. Onak, Organoborane Chemistry, Academic, New York, 1975.

It is interesting that ester, ketone, and nitro groups remain intact during the coupling reaction of pinacolborane at 80°C, though the reaction competes with the hydrogenation of aryl halides (10~20%). The reaction is accelerated in the presence of an electron-donating group, while a withdrawing group slows down the rate of coupling, the electronic effect of which is the reverse of the cross-coupling reactions of diborons and other organoboronic acids. The reaction proceeds through the formation of an (acetoxo)palladium(II) species (110) prior to transmetalation with diboron (Scheme 1-39).

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