Mitsunobu flow: Overcoming batch reactions

Normally when I start a conversation about chemistry that doesn’t work traditionally — batch processes, I begin with questions on heat and pressure — and end up mentioning that microwave won’t offer magic properties to the reaction. But I am impressed with an application note on an intramolecular Mitsunobu with and aromatic NH as the acidic piece in the presence of T3P as an alternative to the list of replacements for DEAD — so imagine my laughter when I read “A solution to DEAD end chemistry.” A really hope they intended that (I’ve run over a thousand of these buggers and sure wish I could have done it this way). Any way to keep this to the story — under normal batch conditions it was reported that the reaction did not proceed. With the Phoenix (ThalesNano) flow reactor, the green alternative T3P and the conditions of high temp and pressure provided a solution to the problems (and 300C was needed for the reaction to proceed). Conditions for the reaction were 300C, 80 bar of pressure with 1 ml/min flow in an 8 ml loop with THF as the solvent. Nice to see a safe method for this reaction since DEAD decomposes violently with heat. Another nice feature I found from the folks at Thales nano — they have placed many of their presentations on slideshare, making it easier to assess the value of applications being used in organic chemistry — absolutely wonderful. Happy Reading!

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