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

Alice Devineau , Guillaume Pousse (1) , Catherine Taillier , Jérôme Blanchet (2) , Jacques Rouden (2) , Vincent Dalla (3)

1 IRSN - Institut de Radioprotection et de Sûreté Nucléaire
2 LCMT - Laboratoire de chimie moléculaire et thioorganique
3 URCOM - Unité de Recherche en Chimie Organique et Macromoléculaire

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.

Mots clés: N-acyliminium; alkylation; electrophilic alcohols; sequential organocatalysis; trichloroacetimidates

Domaines: Chimie organique

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, 2010, 352 (17), pp.2881. ⟨10.1002/adsc.201000602⟩. ⟨hal-00915651⟩