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Ruthenium(II)-Catalyzed C–H (Hetero)Arylation of Alkenylic 1, n -Diazines ( n = 2, 3, and 4): Scope, Mechanism, and Application in Tandem Hydrogenations

Abstract : A general ruthenium(II)-catalyzed methodology enabling the (hetero)arylation of alkenylic C-H bonds utilizing a series of synthetically appealing diazines as directing groups is presented. Despite the presence of additional nitrogen lone pairs remote from the C-H bond activation site, which could eventually poison the catalyst, the reaction times are short (3 hours), thus being suitable for selective double C-H bond arylation. Mixtures of E:Z isomeric products were observed in some cases, which were further hydrogenated in a tandem manner in the presence of the remaining ruthenium catalyst from the first step; representing an alternative approach to more difficult C(sp 3)-H bond functionalization. According to mechanistic studies, the unexpected E:Z product formation seems to occur by thermal C=C bond isomerization after the reduc-tive elimination step.
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https://hal-univ-rennes1.archives-ouvertes.fr/hal-01710194
Contributor : Rafael Gramage-Doria <>
Submitted on : Thursday, May 3, 2018 - 10:14:20 AM
Last modification on : Thursday, March 5, 2020 - 2:05:55 PM
Long-term archiving on: : Tuesday, September 25, 2018 - 9:02:04 PM

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Rafael Gramage-Doria, Sylvain Achelle, Christian Bruneau, Françoise Robin-Le Guen, Vincent Dorcet, et al.. Ruthenium(II)-Catalyzed C–H (Hetero)Arylation of Alkenylic 1, n -Diazines ( n = 2, 3, and 4): Scope, Mechanism, and Application in Tandem Hydrogenations. Journal of Organic Chemistry, American Chemical Society, 2018, 83 (3), pp.1462-1477. ⟨10.1021/acs.joc.7b03024⟩. ⟨hal-01710194⟩

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