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Electrochemical Synthesis of 3a-Bromofuranoindolines and 3a-Bromopyrroloindolines Mediated by MgBr2

preprint
revised on 26.11.2019 and posted on 06.12.2019 by Ju Wu, Hussein Abou Hamdan, Régis Guillot, Cyrille Kouklovsky, Guillaume Vincent

We report an efficient and environmentally friendly electrochemical approach to perform the bromo cyclization of tryptophol, tryptamine and tryptophan derivatives. The 3a-bromofuranoindolines and 3a-bromopyrroloindolines obtained are of interest in the total synthesis of natural products. This dearomative procedure relies on the generation of an electrophilic bromine reagent by the electrochemical oxidation of MgBr2. No organic byproducts are generated with this protocol which avoids the use of an additional electrolyte.

Funding

Chinese Scholarship Council (CSC, PhD fellowship to Ju Wu)

Agence Nationale de la Recherche (ANR-17-CE07-0050; “ArDCo”),

History

Email Address of Submitting Author

guillaume.vincent@u-psud.fr

Institution

Université Paris Sud

Country

France

ORCID For Submitting Author

0000-0003-3162-1320

Declaration of Conflict of Interest

no conflict of interest

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