1,3-Butadienes are important synthons in many synthetic transformations.  We recently reported a facile haloallylation of aryl aldehydes using boron trihalides (Dalton Transactions 2008, 776-778)  A direct elimination of hydrogen halides from the homoallylic halides generated in our previously reported synthesis would facilitate access to a variety of functionalized 1,3-butadienes.   Herein, we wish to report the two-step synthesis of aryl 1, 3-butadienes from aryl aldehydes usingboron trihalide chemistry and 1, 8-diazabicyclo[5.4.0]undec-7-ene.

Synthesis of aryl 1,3-butadienes from the haloallylation of aryl aldehydes using boron trihalide and subsequent elimination with DBU

240th National Meeting (2010)

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