Premium
One‐Pot Hydroxy Group Activation/Carbon‐Carbon Bond Forming Sequence Using a Brønsted Base/Brønsted Acid System
Author(s) -
Devineau Alice,
Pousse Guillaume,
Taillier Catherine,
Blanchet Jérôme,
Rouden Jacques,
Dalla Vincent
Publication year - 2010
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201000602
Subject(s) - chemistry , brønsted–lowry acid–base theory , nucleophile , catalysis , phosphoric acid , enantioselective synthesis , alcohol , alkylation , base (topology) , group (periodic table) , carbon fibers , organic chemistry , medicinal chemistry , combinatorial chemistry , stereochemistry , mathematical analysis , materials science , mathematics , composite number , composite material
A new sequential two‐step multicatalytic strategy is presented consisting in the efficient DBU‐catalysed trichloroacetimidation of an alcohol followed by a ditriflylamine (Tf 2 NH)‐catalysed intermolecular alkylation by silicon‐based nucleophiles and CH 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.