Synthesis of 1,5-diphenylpent-3-en-1-yne derivatives utilizing an aqueous B-alkyl Suzuki cross coupling reaction

1,5-Diphenylpent-3-en-1-yne derivatives were isolated in minor quantities from terrestrial plants and exhibited strong anti-inflammatory activity. A cross coupling reaction between B-benzyl-9-BBN and chloroenynes under mild condition was developed resulting in the formation of different 1,5-diphenyl...

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Bibliographic Details
Published in:Tetrahedron letters 2013-09, Vol.54 (38), p.5162-5166
Main Authors: Chuang, Da-Wei, El-Shazly, Mohamed, Chen, Chin-Chau, Chung, Yu-Ming, D. Barve, Balaji, Wu, Ming-Jung, Chang, Fang-Rong, Wu, Yang-Chang
Format: Article
Language:English
Subjects:
Aqueous reaction
Arrays
B-Alkyl Suzuki coupling
B-Benzyl-9-BBN
Bearing
Cross coupling
Derivatives
Formations
Henna
Palladium
Paving
Synthesis (chemistry)
Tetrahedrons
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Summary:1,5-Diphenylpent-3-en-1-yne derivatives were isolated in minor quantities from terrestrial plants and exhibited strong anti-inflammatory activity. A cross coupling reaction between B-benzyl-9-BBN and chloroenynes under mild condition was developed resulting in the formation of different 1,5-diphenylpent-3-en-1-yne derivatives with a full control on the E/Z selectivity. Several substrates bearing electron-donating and electron-withdrawing substituents were tolerable under the reaction conditions affording the corresponding products in good yields. This is the first study to report the synthesis of a vast array of novel 1,5-diphenylpent-3-en-1-yne derivatives paving the way for the preparation of tailored derivatives on mass scale necessary for biological studies and drug development.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2013.07.020