1. Boron Trihalide Mediated Alkyne-Aldehyde Coupling Reactions: A Mechanistic Investigation.
- Author
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Kabalka, George W., Min-Liang Yao, Borella, Scott, Zhongzhi Wu, Yu-Hong Ju, and Quick, Travis
- Subjects
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BORON compounds , *ALKYNES , *ALDEHYDES , *ORGANIC compounds , *STEREOCHEMISTRY , *CHEMICAL reactions - Abstract
A boron trihalide mediated alkyne-aldehyde coupling reaction leading to stereodefined 1,3,5-triaryl-l,5- dihalo-1,4-pentadienes is described. The study led to the discovery of a direct substitution of hydroxyl groups by stereodefined alkenyl moieties using alkenylboron dihalides. During the investigation, it was also discovered that, at low temperatures, the reaction of BCI3 with alkynes produces monovinylboron dichioride rather than the reported divinylboron chloride. A modified reaction mechanism for the boron trichloride mediated alkyne-aldehyde coupling reaction is now proposed. The reaction temperature and mode of addition have been found to have dramatic affects on the stereochemistry of the diene products. [ABSTRACT FROM AUTHOR]
- Published
- 2008
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