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Synergic Synthesis of Benzannulated Zincabicyclic Complexes, α‐Zincated N Ylides, through Sodium‐TMEDA‐Mediated Zincation of a Haloarene
Author(s) -
Armstrong David R.,
Balloch Liam,
Clegg William,
Dale Sophie H.,
GarcíaÁlvarez Pablo,
Hevia Eva,
Hogg Lorna M.,
Kennedy Alan R.,
Mulvey Robert E.,
O'Hara Charles T.
Publication year - 2009
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200904506
Subject(s) - reagent , chemistry , chlorobenzene , sodium , medicinal chemistry , benzene , ligand (biochemistry) , tetramethylethylenediamine , zinc , combinatorial chemistry , organic chemistry , receptor , catalysis , biochemistry
Double role for sodium: Within a synergic sodium TMP‐zincate reagent, sodium mediates the direct ortho ‐zincation of chlorobenzene and delivers the TMEDA ligand to nucleophilically attack the benzene ring, thereby generating novel open and cyclic zinc zwitterions (example shown). TMP=2,2,6,6‐tetramethylpiperidide; TMEDA= N,N,N′,N′ ‐tetramethylethylenediamine.