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Rhodium-catalyzed oxidative C-H activation/cyclization for the synthesis of phosphaisocoumarins and phosphorous 2-pyrones.
Chemistry. 2013 Nov 25; 19(48):16461-8.C

Abstract

Rhodium-catalyzed cyclization of phosphinic acids and phosphonic monoesters with alkynes has been developed. The oxidative annulation proceeds with complete conversion of phosphinic acid derivatives and allowed the atom-economic preparation of useful phosphaisocoumarins with high yield and selectivity. The reaction is tolerant of extensive substitution on the phosphinic acid, phosphonic monoester and alkyne, including halides, ketone, and hydroxyl groups as substituents. Furthermore, we found that alkenylphosphonic monoesters proceed to give a wide range of phosphorus 2-pyrones through oxidative annulation with alkynes. Mechanistic studies revealed that C-H bond metalation was the rate-limiting step.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Park Y
Department of Chemistry, Kangwon National University, Chuncheon 200-701 (Republic of Korea), Fax: (+82) 33-253-7582.
Seo J
No affiliation info available
Park S
No affiliation info available
Yoo EJ
No affiliation info available
Lee PH
No affiliation info available

MeSH

AlkynesCatalysisCoumarinsCyclizationMolecular StructureOrganophosphorus CompoundsOxidation-ReductionRhodium

Pub Type(s)

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

Language

eng

PubMed ID

24123397

Citation

Park, Youngchul, et al. "Rhodium-catalyzed Oxidative C-H Activation/cyclization for the Synthesis of Phosphaisocoumarins and Phosphorous 2-pyrones." Chemistry (Weinheim an Der Bergstrasse, Germany), vol. 19, no. 48, 2013, pp. 16461-8.
Park Y, Seo J, Park S, et al. Rhodium-catalyzed oxidative C-H activation/cyclization for the synthesis of phosphaisocoumarins and phosphorous 2-pyrones. Chemistry. 2013;19(48):16461-8.
Park, Y., Seo, J., Park, S., Yoo, E. J., & Lee, P. H. (2013). Rhodium-catalyzed oxidative C-H activation/cyclization for the synthesis of phosphaisocoumarins and phosphorous 2-pyrones. Chemistry (Weinheim an Der Bergstrasse, Germany), 19(48), 16461-8. https://doi.org/10.1002/chem.201302652
Park Y, et al. Rhodium-catalyzed Oxidative C-H Activation/cyclization for the Synthesis of Phosphaisocoumarins and Phosphorous 2-pyrones. Chemistry. 2013 Nov 25;19(48):16461-8. PubMed PMID: 24123397.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Rhodium-catalyzed oxidative C-H activation/cyclization for the synthesis of phosphaisocoumarins and phosphorous 2-pyrones. AU - Park,Youngchul, AU - Seo,Jungmin, AU - Park,Sangjune, AU - Yoo,Eun Jeong, AU - Lee,Phil Ho, Y1 - 2013/10/10/ PY - 2013/07/08/received PY - 2013/10/15/entrez PY - 2013/10/15/pubmed PY - 2014/6/13/medline KW - CH activation KW - alkynes KW - annulation KW - cyclization KW - phosphorous heterocycles KW - rhodium SP - 16461 EP - 8 JF - Chemistry (Weinheim an der Bergstrasse, Germany) JO - Chemistry VL - 19 IS - 48 N2 - Rhodium-catalyzed cyclization of phosphinic acids and phosphonic monoesters with alkynes has been developed. The oxidative annulation proceeds with complete conversion of phosphinic acid derivatives and allowed the atom-economic preparation of useful phosphaisocoumarins with high yield and selectivity. The reaction is tolerant of extensive substitution on the phosphinic acid, phosphonic monoester and alkyne, including halides, ketone, and hydroxyl groups as substituents. Furthermore, we found that alkenylphosphonic monoesters proceed to give a wide range of phosphorus 2-pyrones through oxidative annulation with alkynes. Mechanistic studies revealed that C-H bond metalation was the rate-limiting step. SN - 1521-3765 UR - https://www.unboundmedicine.com/medline/citation/24123397/Rhodium_catalyzed_oxidative_C_H_activation/cyclization_for_the_synthesis_of_phosphaisocoumarins_and_phosphorous_2_pyrones_ L2 - https://doi.org/10.1002/chem.201302652 DB - PRIME DP - Unbound Medicine ER -