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

共 69 条

[51] Fimasartan, a novel angiotensin II receptor antagonist [J].

Kim, Je Hak ;

Lee, Joo Han ;

Paik, Soo Heui ;

Kim, Ji Han ;

Chi, Yong Ha .

ARCHIVES OF PHARMACAL RESEARCH, 2012, 35 (07) :1123-1126

[52]

Kozhushkov S.I., 2013, CATAL SCI TECHNOL

[53] New and Improved Manufacturing Process for Valsartan [J].

Kumar, Senthil N. ;

Reddy, Shankar B. ;

Sinha, Brajesh Kumar ;

Mukkanti, Kagga ;

Dandala, Ramesh .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2009, 13 (06) :1185-1189

[54] Direct Arylation of 6-Phenylpurine and 6-Arylpurine Nucleosides by Ruthenium-Catalyzed C-H Bond Activation [J].

Lakshman, Mahesh K. ;

Deb, Ashoke C. ;

Chamala, Raghu Ram ;

Pradhan, Padmanava ;

Pratap, Ramendra .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (48) :11400-11404

[55] Recyclable Solid Ruthenium Catalysts for the Direct Arylation of Aromatic C-H Bonds [J].

Miura, Hiroki ;

Wada, Kenji ;

Hosokawa, Saburo ;

Inoue, Masashi .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (14) :4186-4189

[56] Controlling Site Selectivity in Palladium-Catalyzed C-H Bond Functionalization [J].

Neufeldt, Sharon R. ;

Sanford, Melanie S. .

ACCOUNTS OF CHEMICAL RESEARCH, 2012, 45 (06) :936-946

[57] Ortho-selective direct cross-coupling reaction of 2-aryloxazolines and 2-arylimidazolines with aryl and alkenyl halides catalyzed by ruthenium complexes [J].

Oi, S ;

Aizawa, E ;

Ogino, Y ;

Inoue, Y .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (08) :3113-3119

[58] Ruthenium complex-catalyzed direct ortho arylation and alkenylation of 2-arylpyridines with organic halides [J].

Oi, S ;

Fukita, S ;

Hirata, N ;

Watanuki, N ;

Miyano, S ;

Inoue, Y .

ORGANIC LETTERS, 2001, 3 (16) :2579-2581

[59] Preparative Scale Synthesis of the Biaryl Core of Anacetrapib via a Ruthenium-Catalyzed Direct Arylation Reaction: Unexpected Effect of Solvent Impurity on the Arylation Reaction [J].

Ouellet, Stephane G. ;

Roy, Amelie ;

Molinaro, Carmela ;

Angelaud, Remy ;

Marcoux, Jean-Francois ;

O'Shea, Paul D. ;

Davies, Ian W. .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (05) :1436-1439

[60] Oxidative Coupling of Aromatic Substrates with Alkynes and Alkenes under Rhodium Catalysis [J].

Satoh, Tetsuya ;

Miura, Masahiro .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (37) :11212-11222

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