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Successive Regioselective Metalations of Fused Heterocycles: Synthesis of Polyfunctionalized Furo[3,2-b]pyridines

Abstract : The furopyridine framework was chosen as a target for a lithiation study, in order to define the most effective conditions leading to the total functionalization of the heterocycle. Consequently, a detailed procedure for successive regioselective lithiations/electrophilic trapping of furo[3,2-b]pyridines is described and afforded several polyfunctionalized derivatives in good overall yields. A Pd-catalyzed cross-coupling reaction is also described and easily yielded the 7,7'-bifuro[3,2-b]pyridine.
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https://hal.univ-lorraine.fr/hal-01493935
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Submitted on : Wednesday, March 22, 2017 - 1:53:08 PM
Last modification on : Wednesday, July 17, 2019 - 12:06:02 PM

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Adeline Jasselin-Hinschberger, Corinne Comoy, Anthony Chartoire, Yves Fort. Successive Regioselective Metalations of Fused Heterocycles: Synthesis of Polyfunctionalized Furo[3,2-b]pyridines. Journal of Organic Chemistry, American Chemical Society, 2013, 78 (11), pp.5618-5626. ⟨10.1021/jo400748n⟩. ⟨hal-01493935⟩

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