Abstract
The selective cleavage of carbon–hydrogen bonds in organic compounds is a critical step in many organic syntheses, and is particularly important in the conversion of hydrocarbons to useful organic compounds. An organometallic ruthenium complex can cleave C–H bonds in a variety of aromatic systems, leading to addition to alkenes by C–C bond formation. The catalyst operates with a degree of efficiency, selectivity and generality that will make it extremely valuable in organic synthesis.
This is a preview of subscription content, access via your institution
Access options
Subscribe to this journal
Receive 51 print issues and online access
$199.00 per year
only $3.90 per issue
Buy this article
- Purchase on Springer Link
- Instant access to full article PDF
Prices may be subject to local taxes which are calculated during checkout
Similar content being viewed by others
References
Kleiman, J. P. & Dubeck, M. J. Am. chem. Soc. 85, 1544–1545 (1963).
Chatt, J. & Davidson, J. M. J. chem. Soc. 843–855 (1965).
Webster, D. E. Adv. organomet. Chem. 15, 147–188 (1977).
Shilov, A. E. Activation of Saturated Hydrocarbons by Transition Metal Complexes (Reidel, Dordrecht, 1984).
Crabtree, R. H. Chem. Rev. 85, 245–269 (1985).
Jones, W. D. & Ferher, F. J. Accts. chem. Res. 22, 91–100 (1989).
Hill, C. L. Activation and Functionalization of Alkanes (Wiley, London, 1991).
Bruce, M. I. Angew. Chem., Int. Edn. engl. 18, 73–86 (1977).
Newkome, G. R., Puckett, W. E., Gupta, V. K. & Kiefer, G. E. Chem. Rev. 86, 451–489 (1986).
Ryabov, A. D. Chem. Rev. 90, 403–424 (1990).
Jordan, R. F. & Taylor, D. F. J. Am. chem. Soc. 111, 778–779 (1989).
Moore, E. J. et al. J. Am. chem. Soc. 114, 5888–5890 (1992).
Levison, J. J. & Robinson, S. D. J. chem. Soc., A 2947–2954 (1970).
Knobler, C. B., Crawford, S. S. & Kaesz, H. D. lnorg. Chem. 14, 2062–2066 (1975).
McGuiggan, M. F. & Pignolet, L. H. lnorg. Chem. 21, 2523–2526 (1982).
Hong, P. & Yamazaki, H. J. molec. Catalysis. 26, 297–311 (1984).
Komiya, S. & Yamamoto, A. Chem. Lett. 475–478 (1975).
Cambie, R. C., Metzler, M. R., Rutledge, P. S. & Woodgate, P. D. J. organomet. Chem. 429, 59–86 (1992).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Murai, S., Kakiuchi, F., Sekine, S. et al. Efficient catalytic addition of aromatic carbon-hydrogen bonds to olefins. Nature 366, 529–531 (1993). https://doi.org/10.1038/366529a0
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1038/366529a0
This article is cited by
-
A directed enolization strategy enables by-product-free construction of contiguous stereocentres en route to complex amino acids
Nature Chemistry (2024)
-
Suzuki–Miyaura cross-couplings for alkyl boron reagent: recent developments—a review
Future Journal of Pharmaceutical Sciences (2023)
-
Synthetic DNA applications in information technology
Nature Communications (2022)
-
Transition metal-catalysed directed C–H functionalization with nucleophiles
Nature Synthesis (2022)
-
Catalyst-transfer system in stoichiometry-independent AA+BB-type Migita–Kosugi–Stille coupling polycondensation using ester-functionalized dibromo monomer
Polymer Journal (2022)
Comments
By submitting a comment you agree to abide by our Terms and Community Guidelines. If you find something abusive or that does not comply with our terms or guidelines please flag it as inappropriate.