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Rhodium N-heterocyclic carbene-catalyzed [4 + 2] and [5 + 2] cycloaddition reactions.
J Org Chem. 2006 Jan 06; 71(1):91-6.JO

Abstract

[reactions: see text] A rhodium complex of N-heterocyclic carbene (NHC) has been developed for intra- and intermolecular [4 + 2] and intramolecular [5 + 2] cycloaddition reactions. This is the first use of a transition-metal NHC complex in a Diels-Alder-type reaction. For the intramolecular [4 + 2] cycloaddition reactions, all the dienynes studied were converted to their corresponding cycloadducts in 91-99% yields within 10 min. Moreover, up to 1900 turnovers have been obtained for the intramolecular [4 + 2] cycloaddition at 15-20 degrees C. For the intermolecular [4 + 2] cycloadditions, high yields (71-99%) of the corresponding cycloaddition products were obtained. The reaction time and yield were highly dependent upon the diene and the dienophile. For the intramolecular [5 + 2] cycloaddition reactions, all the alkyne vinylcyclopropanes studied were converted to their corresponding cycloadducts in 91-98% yields within 10 min. However, the catalytic system was not effective for an intermolecular [5 + 2] cycloaddition reaction.

Authors+Show Affiliations

Lee SI
Intelligent Textile System Research Center, Department of Chemistry, College of Natural Sciences, Seoul National University, Seoul 151-747, Korea.
Park SY
No affiliation info available
Park JH
No affiliation info available
Jung IG
No affiliation info available
Choi SY
No affiliation info available
Chung YK
No affiliation info available
Lee BY
No affiliation info available

MeSH

CatalysisCyclizationHydrocarbonsMagnetic Resonance SpectroscopyMethaneMolecular StructureRhodium

Pub Type(s)

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

Language

eng

PubMed ID

16388622

Citation

Lee, Sang Ick, et al. "Rhodium N-heterocyclic Carbene-catalyzed [4 + 2] and [5 + 2] Cycloaddition Reactions." The Journal of Organic Chemistry, vol. 71, no. 1, 2006, pp. 91-6.
Lee SI, Park SY, Park JH, et al. Rhodium N-heterocyclic carbene-catalyzed [4 + 2] and [5 + 2] cycloaddition reactions. J Org Chem. 2006;71(1):91-6.
Lee, S. I., Park, S. Y., Park, J. H., Jung, I. G., Choi, S. Y., Chung, Y. K., & Lee, B. Y. (2006). Rhodium N-heterocyclic carbene-catalyzed [4 + 2] and [5 + 2] cycloaddition reactions. The Journal of Organic Chemistry, 71(1), 91-6.
Lee SI, et al. Rhodium N-heterocyclic Carbene-catalyzed [4 + 2] and [5 + 2] Cycloaddition Reactions. J Org Chem. 2006 Jan 6;71(1):91-6. PubMed PMID: 16388622.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Rhodium N-heterocyclic carbene-catalyzed [4 + 2] and [5 + 2] cycloaddition reactions. AU - Lee,Sang Ick, AU - Park,Se Yeoun, AU - Park,Ji Hoon, AU - Jung,Il Gu, AU - Choi,Soo Young, AU - Chung,Young Keun, AU - Lee,Bun Yeoul, PY - 2006/1/4/pubmed PY - 2006/7/27/medline PY - 2006/1/4/entrez SP - 91 EP - 6 JF - The Journal of organic chemistry JO - J Org Chem VL - 71 IS - 1 N2 - [reactions: see text] A rhodium complex of N-heterocyclic carbene (NHC) has been developed for intra- and intermolecular [4 + 2] and intramolecular [5 + 2] cycloaddition reactions. This is the first use of a transition-metal NHC complex in a Diels-Alder-type reaction. For the intramolecular [4 + 2] cycloaddition reactions, all the dienynes studied were converted to their corresponding cycloadducts in 91-99% yields within 10 min. Moreover, up to 1900 turnovers have been obtained for the intramolecular [4 + 2] cycloaddition at 15-20 degrees C. For the intermolecular [4 + 2] cycloadditions, high yields (71-99%) of the corresponding cycloaddition products were obtained. The reaction time and yield were highly dependent upon the diene and the dienophile. For the intramolecular [5 + 2] cycloaddition reactions, all the alkyne vinylcyclopropanes studied were converted to their corresponding cycloadducts in 91-98% yields within 10 min. However, the catalytic system was not effective for an intermolecular [5 + 2] cycloaddition reaction. SN - 0022-3263 UR - https://www.unboundmedicine.com/medline/citation/16388622/Rhodium_N_heterocyclic_carbene_catalyzed_[4_+_2]_and_[5_+_2]_cycloaddition_reactions_ DB - PRIME DP - Unbound Medicine ER -