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Critical ligand and salt effects in organomagnesiate‐promoted 3,3‐disubstituted phthalides synthesis from 2‐iodobenzoate derivatives

Abstract : Phthalides, also called isobenzofuranones, are widespread in many biologically active compounds and natural products. To date, most of their synthetic routes are non-convergent. Herein we report a convergent route using a metal halogen exchange (MHE) strategy. Indeed MHE of easily available 2-iodobenzoate derivatives, using the bimetallic organomagnesiate complex (rac)-(BIPHEN)BuMgLi, where (rac)-BIPHEN is (rac)-5,5′,6,6′-tetramethyl-3,3′-di-t-butyl-1,1′-biphenyl-2,2′-diol, followed by addition of a ketone which lead to an intramolecular cyclisation, and the formation of a series of diverse 3,3-disubstituted isobenzofuranones in good yield. Among the several MHE agents investigated, (rac)-(BIPHEN)BuMgLi was the only one to make such a process possible with full tolerance of various reactive functional substituents useful for subsequent transformations. The synthetic pathway to access the magnesiate has been found to play a prominent role in its reactivity. Therefore, the bimetallic magnesiate complex has been characterized by solution-state 1H, 7Li and 1H DOSY NMR experiments.
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https://hal.archives-ouvertes.fr/hal-03325715
Contributor : Philippe C. Gros Connect in order to contact the contributor
Submitted on : Friday, January 14, 2022 - 1:59:48 PM
Last modification on : Saturday, January 15, 2022 - 3:45:14 AM

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Sabrina Touchet, Callum Yeardley, Charles O’hara, Philippe Gros. Critical ligand and salt effects in organomagnesiate‐promoted 3,3‐disubstituted phthalides synthesis from 2‐iodobenzoate derivatives. European Journal of Organic Chemistry, Wiley-VCH Verlag, 2021, 2021 (34), pp.4835-4845. ⟨10.1002/ejoc.202100899⟩. ⟨hal-03325715v2⟩

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