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Intermolecular coupling of alkenes to heterocycles via C-H bond activation.
J Org Chem. 2004 Oct 15; 69(21):7329-35.JO

Abstract

The intermolecular coupling of unactivated alkenes to a range of heterocycles using a Rh(I) catalyst was investigated. A variety of functional groups were incorporated into the alkene, including esters, nitriles, acetals, and phthalimide. Furthermore, the heterocycle tolerated substitution with both electron-rich and electron-deficient groups. The intermolecular coupling became possible after it was discovered that weak acids dramatically increase the rate of both the inter- and intramolecular reactions. An extensive optimization of additives was performed, and HCl.PCy(3) (Cy = cyclohexyl) and HCl.P-t-Bu(2)Et were in general found to be the best additives for the reaction.

Authors+Show Affiliations

Department of Chemistry, University of California and Division of Chemical Sciences, Lawrence Berkeley National Laboratory, Berkeley, California 94720, USA.No affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.
Research Support, U.S. Gov't, P.H.S.

Language

eng

PubMed ID

15471487

Citation

Tan, Kian L., et al. "Intermolecular Coupling of Alkenes to Heterocycles Via C-H Bond Activation." The Journal of Organic Chemistry, vol. 69, no. 21, 2004, pp. 7329-35.
Tan KL, Park S, Ellman JA, et al. Intermolecular coupling of alkenes to heterocycles via C-H bond activation. J Org Chem. 2004;69(21):7329-35.
Tan, K. L., Park, S., Ellman, J. A., & Bergman, R. G. (2004). Intermolecular coupling of alkenes to heterocycles via C-H bond activation. The Journal of Organic Chemistry, 69(21), 7329-35.
Tan KL, et al. Intermolecular Coupling of Alkenes to Heterocycles Via C-H Bond Activation. J Org Chem. 2004 Oct 15;69(21):7329-35. PubMed PMID: 15471487.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Intermolecular coupling of alkenes to heterocycles via C-H bond activation. AU - Tan,Kian L, AU - Park,Steve, AU - Ellman,Jonathan A, AU - Bergman,Robert G, PY - 2004/10/9/pubmed PY - 2004/12/23/medline PY - 2004/10/9/entrez SP - 7329 EP - 35 JF - The Journal of organic chemistry JO - J Org Chem VL - 69 IS - 21 N2 - The intermolecular coupling of unactivated alkenes to a range of heterocycles using a Rh(I) catalyst was investigated. A variety of functional groups were incorporated into the alkene, including esters, nitriles, acetals, and phthalimide. Furthermore, the heterocycle tolerated substitution with both electron-rich and electron-deficient groups. The intermolecular coupling became possible after it was discovered that weak acids dramatically increase the rate of both the inter- and intramolecular reactions. An extensive optimization of additives was performed, and HCl.PCy(3) (Cy = cyclohexyl) and HCl.P-t-Bu(2)Et were in general found to be the best additives for the reaction. SN - 0022-3263 UR - https://www.unboundmedicine.com/medline/citation/15471487/Intermolecular_coupling_of_alkenes_to_heterocycles_via_C_H_bond_activation_ L2 - https://doi.org/10.1021/jo048666p DB - PRIME DP - Unbound Medicine ER -