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Extra info for Catalytic Heterofunctionalization 2005
Addition of silylborane (88)  and stannylborane (90)  to 1,3-dienes with a nickel(0) or palladium(0) complex affords analogous 1,4-addition products in high yields. 3 Metal-Catalyted Diboration, Silylboration and Stannylboration Pt(C2H4)(PPh3)2 octane, reflux Ph PhMe2SiO R + PhMe2Si-Bpin + RCHO R=Ph, 79% (syn/anti=99/1) R=C6H13, 71% (syn/anti=93/7) 88 Scheme 1-25 Pt Bpin SiMe2Ph SiMe2Ph pinB SiMe2Ph Pt Ph Pt RCHO pinB O Ph R Ph Scheme 1-35 106 Ph Bpin Allylation of Aldehydes nately not sufficiently regioselective and suffers from stereochemical isomerization, but the stannylboration yields a single product by selective migration of the boryl group to the less-substituted double bond.
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. (b) B.
It is hoped that further innovative synthetic chemistry in diverse areas, stimulated by the metal-catalyzed methodology, will appear in the future. Abbreviations cod coe nbd dba Cy Py Cp Cp* 1,5-cyclooctadiene cyclooctene norbornadiene dibenzalacetone cyclohexyl pyridine η5-C5H5 η5-Me5C5 etpo TTMPP dppf dppm dppe dppp dppb P(OCH2)3CCH2CH3 tris(2,4,6-trimethoxyphenyl)phosphine, 1,1′-bis(diphenylphosphino)ferrocene Ph2PCH2PPh2 Ph2P(CH2)2PPh2 Ph2P(CH2)3PPh2 Ph2P(CH2)4PPh2 39 40 1 Hydroboration, Diboration, Silylboration and Stannylboration References 1 Reviews for catalyzed hydroboration, see: (a) L.