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Transforming LiTMP Lithiation of Challenging Diazines through Gallium Alkyl Trans‐Metal‐Trapping
Author(s) -
Uzelac Marina,
Kennedy Alan R.,
Hevia Eva,
Mulvey Robert E.
Publication year - 2016
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.201607284
Subject(s) - benzothiazole , deprotonation , pyrazine , alkyl , chemistry , pyridazine , regioselectivity , gallium , trapping , pyrimidine , medicinal chemistry , tandem , metal , combinatorial chemistry , stereochemistry , organic chemistry , catalysis , materials science , ion , ecology , composite material , biology
This study establishes a new trans‐metal‐trapping (TMT) procedure based on a mixture of LiTMP (the base) and tris(trimethylsilylmethyl)gallium [Ga(CH 2 SiMe 3 ) 3 , GaR 3 ] (the trap) that, operating in a tandem manner, is effective for the regioselective deprotonation of sensitive diazines in hydrocarbon solution, as illustrated through reactions of pyrazine, pyridazine, and pyrimidine, as well as through the N‐S heterocycle benzothiazole. The metallo‐activated complexes of all of these compounds were isolated and structurally defined.