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Rhodium-catalyzed intermolecular [2 + 2] cycloaddition of terminal alkynes with electron-deficient alkenes.
Org Lett. 2013 Mar 01; 15(5):1024-7.OL

Abstract

The first catalytic intermolecular [2 + 2] cycloaddition of terminal alkynes with electron-deficient alkenes is reported. The reaction proceeds with an 8-quinolinolato rhodium/phosphine catalyst system to give cyclobutenes from various substrates having polar functional groups in high yields with complete regioselectivity.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Sakai K
Department of Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, Kanagawa 223-8522, Japan.
Kochi T
No affiliation info available
Kakiuchi F
No affiliation info available

MeSH

AlkenesAlkynesCatalysisCycloaddition ReactionCyclobutanesMolecular StructureRhodiumStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

23398205

Citation

Sakai, Kazunori, et al. "Rhodium-catalyzed Intermolecular [2 + 2] Cycloaddition of Terminal Alkynes With Electron-deficient Alkenes." Organic Letters, vol. 15, no. 5, 2013, pp. 1024-7.
Sakai K, Kochi T, Kakiuchi F. Rhodium-catalyzed intermolecular [2 + 2] cycloaddition of terminal alkynes with electron-deficient alkenes. Org Lett. 2013;15(5):1024-7.
Sakai, K., Kochi, T., & Kakiuchi, F. (2013). Rhodium-catalyzed intermolecular [2 + 2] cycloaddition of terminal alkynes with electron-deficient alkenes. Organic Letters, 15(5), 1024-7. https://doi.org/10.1021/ol303510k
Sakai K, Kochi T, Kakiuchi F. Rhodium-catalyzed Intermolecular [2 + 2] Cycloaddition of Terminal Alkynes With Electron-deficient Alkenes. Org Lett. 2013 Mar 1;15(5):1024-7. PubMed PMID: 23398205.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Rhodium-catalyzed intermolecular [2 + 2] cycloaddition of terminal alkynes with electron-deficient alkenes. AU - Sakai,Kazunori, AU - Kochi,Takuya, AU - Kakiuchi,Fumitoshi, Y1 - 2013/02/11/ PY - 2013/2/13/entrez PY - 2013/2/13/pubmed PY - 2013/7/3/medline SP - 1024 EP - 7 JF - Organic letters JO - Org Lett VL - 15 IS - 5 N2 - The first catalytic intermolecular [2 + 2] cycloaddition of terminal alkynes with electron-deficient alkenes is reported. The reaction proceeds with an 8-quinolinolato rhodium/phosphine catalyst system to give cyclobutenes from various substrates having polar functional groups in high yields with complete regioselectivity. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/23398205/Rhodium_catalyzed_intermolecular_[2_+_2]_cycloaddition_of_terminal_alkynes_with_electron_deficient_alkenes_ L2 - https://doi.org/10.1021/ol303510k DB - PRIME DP - Unbound Medicine ER -