Abstract
Corey-Fuchs olefination is a two-step reaction, involving the reaction of an aldehyde and tetrabromomethane (CBr4) in the presence of the triphenylphosphine (Ph3P) to synthesize 1,1-dibromoolefins. In the second step, the conversion of the dibromoolefins to alkynes occurred in the presence of n-BuLi as the base. This transformation was first discovered by E. J. Corey and P. L. Fuchs in 1972. Due to the importance of terminal alkynes in the synthetic organic chemistry, the Corey-Fuchs reaction has found many applications in organic transformations; particularly in the total synthesis of several biologically active natural products, often as starting materials.
Keywords: Corey-Fuchs, Olefination, 1, 1-Dibromoolefins, Total synthesis, Organic synthesis, Terminal alkynes, Triphenylphosphine.
Graphical Abstract
Current Organic Chemistry
Title:Developments of Corey-Fuchs Reaction in Organic and Total Synthesis of Natural Products
Volume: 19 Issue: 22
Author(s): Majid M. Heravi, Shima Asadi, Niousha Nazari and Boshra Malekzadeh Lashkariani
Affiliation:
Keywords: Corey-Fuchs, Olefination, 1, 1-Dibromoolefins, Total synthesis, Organic synthesis, Terminal alkynes, Triphenylphosphine.
Abstract: Corey-Fuchs olefination is a two-step reaction, involving the reaction of an aldehyde and tetrabromomethane (CBr4) in the presence of the triphenylphosphine (Ph3P) to synthesize 1,1-dibromoolefins. In the second step, the conversion of the dibromoolefins to alkynes occurred in the presence of n-BuLi as the base. This transformation was first discovered by E. J. Corey and P. L. Fuchs in 1972. Due to the importance of terminal alkynes in the synthetic organic chemistry, the Corey-Fuchs reaction has found many applications in organic transformations; particularly in the total synthesis of several biologically active natural products, often as starting materials.
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Cite this article as:
M. Heravi Majid, Asadi Shima, Nazari Niousha and Malekzadeh Lashkariani Boshra, Developments of Corey-Fuchs Reaction in Organic and Total Synthesis of Natural Products, Current Organic Chemistry 2015; 19 (22) . https://dx.doi.org/10.2174/1385272819666150619174010
DOI https://dx.doi.org/10.2174/1385272819666150619174010 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
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