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

被引：44

作者：

Diers, Emelyne ^{[1
]}

Kumar, N. Y. Phani ^{[1
]}

Mejuch, Tom ^{[2
]}

Marek, Ilan ^{[2
]}

Ackermann, Lutz ^{[1
]}

机构：

[1] Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany

[2] Technion Israel Inst Technol, Schulich Fac Chem, IL-32000 Haifa, Israel

来源：

TETRAHEDRON | 2013年 / 69卷 / 22期

基金：

欧洲研究理事会;

关键词：

ARB; Arylation; C-H activation; Ruthenium; Valsartan; CATALYZED DIRECT ARYLATIONS; II RECEPTOR ANTAGONISTS; BOND ACTIVATION; ARYL; PALLADIUM; ARENES; POTENT; ALKENYLATION; ALKYLATION; EFFICIENT;

D O I：

10.1016/j.tet.2013.01.006

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：4445 / 4453

页数：9

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