Stereospecific preparation of symmetrical (1Z,3Z) 2,3-difluoro-1,4-disubstituted-buta-1,3-dienes by the coupling reaction between bis(tributyltin) and high E/Z 1-bromo-1-fluoroalkenes
โ Scribed by Jianjun Xu; Donald J Burton
- Publisher
- Elsevier Science
- Year
- 2002
- Tongue
- French
- Weight
- 73 KB
- Volume
- 43
- Category
- Article
- ISSN
- 0040-4039
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โฆ Synopsis
When the palladium-catalyzed coupling reaction of Bu 3 SnSnBu 3 and high E/Z 1-bromo-1-fluoroalkenes is carried out at room temperature, symmetrical (1Z,3Z) 2,3-difluorinated-1,4-disubstituted-buta-1,3-dienes are successfully prepared in good yields.
๐ SIMILAR VOLUMES
A new synthesis of stereodefined 1-trimeUlylsllyl-1,3-dlenes is described. The method is based on two sequential coupling reactions between Grlgnard reagents and the readily available (Z)-or (15)-l -bromo-2-phenylthloethene, In the presence of transition metal catalysts.
1-Alkenyldibromoboranes readily obtainable by the hydroboration of first alkyneswith dibromoborane-dimethyl sulfide followed by treatment with tribromoborane, react without any difficulty with second 1-alkynes as bromoborating agents to give (l-alkenyl)(Z-bromo-l-alkeny)bromoboranes (5). The reactio