Chromenes through Metal-Catalyzed Reactions of Styrenyl Ethers. Mechanism and Utility in Synthesis
Publication type: Journal Article
Publication date: 1998-03-01
scimago Q1
wos Q1
SJR: 5.554
CiteScore: 22.5
Impact factor: 15.6
ISSN: 00027863, 15205126
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
Abstract
An efficient metal-catalyzed process that converts styrenyl ethers to 2-substituted chromenes is described. This class of reactions may be carried out on either terminal or disubstituted styrenyl substrates. Depending on the level of substitution of the olefins, the Ru−carbene catalyst may initiate reaction either by interaction with the styrenyl or the carbocyclic alkene. Metal-catalyzed rearrangements, carried out under an atmosphere of ethylene, afford excellent yields of monomeric products. With disubstituted styrene ethers, the presence of ethylene is also critical to reaction efficiency. Mechanistic data that rationalize these observations are provided. Although Ru complexes (PCy3)2Cl2RuCHCHCPh2 or (PCy3)2Cl2RuCHPh effectively serve as catalysts, with the more functionalized substrates, higher yields are obtained when Mo(CHCMe2Ph)(N(2,6-(i-Pr)2C6H3))(OCMe(CF3)2)2 is used. A variety of starting materials for the metal-catalyzed chromene synthesis (disubstituted styrenes) are available in the opticall...
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144
Total citations:
144
Citations from 2024:
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(4.16%)
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Harrity J. P. A. et al. Chromenes through Metal-Catalyzed Reactions of Styrenyl Ethers. Mechanism and Utility in Synthesis // Journal of the American Chemical Society. 1998. Vol. 120. No. 10. pp. 2343-2351.
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Harrity J. P. A., La D. S., Cefalo D. R., Visser M. S., Hoveyda A. H. Chromenes through Metal-Catalyzed Reactions of Styrenyl Ethers. Mechanism and Utility in Synthesis // Journal of the American Chemical Society. 1998. Vol. 120. No. 10. pp. 2343-2351.
Cite this
RIS
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TY - JOUR
DO - 10.1021/ja9739796
UR - https://doi.org/10.1021/ja9739796
TI - Chromenes through Metal-Catalyzed Reactions of Styrenyl Ethers. Mechanism and Utility in Synthesis
T2 - Journal of the American Chemical Society
AU - Harrity, Joseph P. A.
AU - La, Daniel S
AU - Cefalo, Dustin R
AU - Visser, Michael S
AU - Hoveyda, Amir H.
PY - 1998
DA - 1998/03/01
PB - American Chemical Society (ACS)
SP - 2343-2351
IS - 10
VL - 120
SN - 0002-7863
SN - 1520-5126
ER -
Cite this
BibTex (up to 50 authors)
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@article{1998_Harrity,
author = {Joseph P. A. Harrity and Daniel S La and Dustin R Cefalo and Michael S Visser and Amir H. Hoveyda},
title = {Chromenes through Metal-Catalyzed Reactions of Styrenyl Ethers. Mechanism and Utility in Synthesis},
journal = {Journal of the American Chemical Society},
year = {1998},
volume = {120},
publisher = {American Chemical Society (ACS)},
month = {mar},
url = {https://doi.org/10.1021/ja9739796},
number = {10},
pages = {2343--2351},
doi = {10.1021/ja9739796}
}
Cite this
MLA
Copy
Harrity, Joseph P. A., et al. “Chromenes through Metal-Catalyzed Reactions of Styrenyl Ethers. Mechanism and Utility in Synthesis.” Journal of the American Chemical Society, vol. 120, no. 10, Mar. 1998, pp. 2343-2351. https://doi.org/10.1021/ja9739796.