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.
Links
MeSH
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 - CH 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 -