Transforming LiTMP Lithiation of Challenging Diazines through Gallium Alkyl Trans‐Metal‐Trapping | Zendy

Uzelac Marina | Zendy; Kennedy Alan R. | Zendy; Hevia Eva | Zendy; Mulvey Robert E. | Zendy

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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 , chemistry , pyrazine , pyridazine , alkyl , regioselectivity , gallium , pyrimidine , metal , combinatorial chemistry , medicinal chemistry , tandem , trapping , stereochemistry , organic chemistry , catalysis , materials science , ion , ecology , composite material , biology

Abstract 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.

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