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C(sp 2 )−Si Bond Functionalization through Intramolecular Activation by Alkoxides
Author(s) -
Curpanen Sebastien,
Poli Giovanni,
Oble. Julie,
PerezLuna Alejandro
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202001458
Subject(s) - chemistry , organosilicon , electrophile , intramolecular force , surface modification , reactivity (psychology) , silylation , reagent , combinatorial chemistry , substitution reaction , stereochemistry , organic chemistry , catalysis , medicine , alternative medicine , pathology
Organosilicon reagents are invaluable tools in the hands of the modern chemist that allow accomplishing a number of synthetically useful transformations. While some are standard reactions, others are more complex transformations, such as the Brook rearrangement and its variants. This carbon‐to‐oxygen silyl migration represents a privileged method to generate transient carbanionic species well suited to undergo functionalization upon electrophilic substitution in the presence of an electrophile. This minireview focuses on recent advances in C(sp 2 )−Si bond functionalization through intramolecular activation by alkoxides. The key elements of reactivity will be highlighted in the introduction to allow the proper understanding of the migration process. Then, an overview of the reactivity of substrates incorporating the C(sp 2 )−Si motif and their synthetic applications will be provided.