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One-Pot Hydroxy Group Activation/Carbon-Carbon Bond Forming Sequence Using a Brønsted Base/Brønsted Acid System

Abstract : A new sequential two-step multicatalytic strategy is presented consisting in the efficient DBU-catalysed trichloroacetimidation of an alcohol followed by a ditriflylamine (Tf2NH)-catalysed intermolecular alkylation by silicon-based nucleophiles and C[BOND]H nucleophiles. The distinct feature of the trichloroacetimidate group allows use of weaker acid catalysts such as 1,1′-bi-2-naphthol (BINOL)-derived phosphoric acid, pointing out the possible development of an enantioselective variant. This unprecedented sequential one-pot Brønsted base-Brønsted acid catalysis further expands the synthetic scope of the trichloroacetimidate group.
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https://hal.archives-ouvertes.fr/hal-00915651
Contributor : Jérôme Blanchet Connect in order to contact the contributor
Submitted on : Monday, December 9, 2013 - 10:48:17 AM
Last modification on : Monday, August 29, 2022 - 2:34:07 PM

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Alice Devineau, Guillaume Pousse, Catherine Taillier, Jérôme Blanchet, Jacques Rouden, et al.. One-Pot Hydroxy Group Activation/Carbon-Carbon Bond Forming Sequence Using a Brønsted Base/Brønsted Acid System. Advanced Synthesis and Catalysis, Wiley-VCH Verlag, 2010, 352 (17), pp.2881. ⟨10.1002/adsc.201000602⟩. ⟨hal-00915651⟩

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