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Carboxylate-assisted ruthenium(II)-catalyzed C–H arylations of 5-aryl tetrazoles: step-economical access to Valsartan

Carboxylate assistance was key to success for highly efficient ruthenium-catalyzed direct ortho-arylations of tetrazolyl-substituted arenes with aryl halides and triflates in the absence of phosphine ligands. Thus, ruthenium(II) biscarboxylates allowed for C–H bond functionalizations with excellent...

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Bibliographic Details
Published in:Tetrahedron 2013-06, Vol.69 (22), p.4445-4453
Main Authors: Diers, Emelyne, Phani Kumar, N.Y., Mejuch, Tom, Marek, Ilan, Ackermann, Lutz
Format: Article
Language:English
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Summary:Carboxylate assistance was key to success for highly efficient ruthenium-catalyzed direct ortho-arylations of tetrazolyl-substituted arenes with aryl halides and triflates in the absence of phosphine ligands. Thus, ruthenium(II) biscarboxylates allowed for C–H bond functionalizations with excellent chemo- and site-selectivities, which set the stage for an atom- and step-economical access to key angiotensin-II-receptor blockers. Mechanistic studies revealed the C–H bond metalation to be reversible, and were suggestive of a rate-determining reductive elimination. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2013.01.006