Angewandte Chemie International Edition in English

Volume 24, Issue 10 pp. 878-879

Communication

Full Access

Catalytic Hydroboration with Rhodium Complexes

Detlef Männig M. Sc.,

Detlef Männig M. Sc.

Institut für Anorganische Chemie der Universität, Meiserstrasse 1, D-8000 München 2 (FRG)

Search for more papers by this author

Prof. Dr. Heinrich Nöth,

Corresponding Author

Prof. Dr. Heinrich Nöth

Institut für Anorganische Chemie der Universität, Meiserstrasse 1, D-8000 München 2 (FRG)

Institut für Anorganische Chemie der Universität, Meiserstrasse 1, D-8000 München 2 (FRG)Search for more papers by this author

Detlef Männig M. Sc.,

Detlef Männig M. Sc.

Institut für Anorganische Chemie der Universität, Meiserstrasse 1, D-8000 München 2 (FRG)

Search for more papers by this author

Prof. Dr. Heinrich Nöth,

Corresponding Author

Prof. Dr. Heinrich Nöth

Institut für Anorganische Chemie der Universität, Meiserstrasse 1, D-8000 München 2 (FRG)

Institut für Anorganische Chemie der Universität, Meiserstrasse 1, D-8000 München 2 (FRG)Search for more papers by this author

First published: October 1985

https://doi.org/10.1002/anie.198508781

Citations: 476

About

PDF

Tools

Share a link

Email
Wechat
Bluesky

Graphical Abstract

The activation of CC double bonds for hydroboration may be achieved using rhodium complexes: e.g., the dioxaborole 1 undergoes preferential addition to the double bond when [CIRh(PPh₃)₃] is added to the reaction mixture.

References

1 J. L. Speier, Adv. Organomet. Chem. 17 (1979) 407;
10.1016/S0065-3055(08)60328-7
CAS Google Scholar
C. S. Cundy, B. M. Kingston, M. F. Lappert, Adv. Organomet. Chem. 11 (1973) 297.
Google Scholar
2 E. S. Brown, Aspects Homogeneous Catal. 2 (1974) 57.
10.1007/978-94-010-2285-9_2
CAS Google Scholar
3 H. C. Brown: Organic Synthesis via Boranes, Wiley-Interscience, New York 1975.
Google Scholar
4 Catalytic hydroborations with polyboranes or Rh-carbaboranes: T. Davan, E. W. Corcoran, L. G. Sneddon, Organometallics 2 (1982) 1963;
Google Scholar
R. Wilczynski, L. G. Sneddon, Inorg. Chem. 20 (1981) 3955;
10.1021/ic50225a071
CAS Web of Science® Google Scholar
J. D. Hewes, C. W. Kreimendahl, T. B. Marder, M. F. Hawthorne, J. Am. Chem. Soc. 106 (1984) 5757.
10.1021/ja00331a072
CAS Web of Science® Google Scholar
5 H. C. Brown, S. K. Gupta, J. Am. Chem. Soc. 93 (1971) 1816.
10.1021/ja00736a061
CAS Web of Science® Google Scholar
6 For the relative reactivity of unsaturated functional groups toward boranes, see [3]. The aldehyde group is much more reactive than the keto group.
Google Scholar
7 H. Kono, K. Ito, Chem. Lett. 1975, 1095. We have synthesized [{(C₆H₅)₃P}₂Rh(H)Cl(BO₂C₆H₄)] from 1 and [ClRh{P(C₆H₅)₃}₃] in benzene in 57% yield: IR: V(RhH) = 2130 cm⁻¹; ¹¹B-NMR (CD₂Cl₂): δ = 37.7; ¹H-NMR (CD₂Cl₂): δ = 7.8–6.6 (m, 34H), - 14.65 (dt, 1 H, J(RhH) = 27, ² J(PH) = 14 Hz); m.p. = 78°C (decomp.).
Google Scholar
8 We will report elsewhere further evidence for the proposed mechanism and on the reduction of the olefinic double bond in the presence of other functional groups (e.g., epoxides).
Google Scholar

Citing Literature

Volume24, Issue10

October 1985

Pages 878-879

Catalytic Hydroboration with Rhodium Complexes

Graphical Abstract

References

Citing Literature

References

Information

About Wiley Online Library

Help & Support

Opportunities

Connect with Wiley

Catalytic Hydroboration with Rhodium Complexes

Graphical Abstract

References

Citing Literature

References

Related

Information