Tags

Type your tag names separated by a space and hit enter

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

Tan KL
Department of Chemistry, University of California and Division of Chemical Sciences, Lawrence Berkeley National Laboratory, Berkeley, California 94720, USA.
Park S
No affiliation info available
Ellman JA
No affiliation info available
Bergman RG
No affiliation info available

MeSH

AlkenesCatalysisCyclizationHeterocyclic CompoundsMolecular StructureRhodiumSolvents

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_ DB - PRIME DP - Unbound Medicine ER -