4.4 Article

Organometallic alkylation of 2-chloro-4,6-dimethoxy-1,3,5-triazine: a study

Journal

TETRAHEDRON
Volume 61, Issue 18, Pages 4475-4483

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2005.02.085

Keywords

2-chloro-4,6-diniethoxy-1,3,5-triazine; organometallics; coupling reactions; palladium and nickel catalysts

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The reactivity of 2-chloro-4,6-dimethoxy-1,3,5-triazine (1) has been investigated in Pd- or Ni-catalyzed cross-coupling processes with organostannanes, Grignard reagents, organoalanes and organozinc halides. All organometallic reagents considered form new C-C bonds on the heteroaromatic ring and afford the corresponding 2-alkyl-4,6-dimethoxy-1,3,5-triazines in moderate to very good yields. The collected data allows the choice of the alkylating agent as well as the experimental conditions depending on the residue to transfer. (c) 2005 Elsevier Ltd. All rights reserved.

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