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

[21] Transition-metal-catalyzed direct arylations via C-H bond cleavages [J].

Ackermann, Lutz .

PURE AND APPLIED CHEMISTRY, 2010, 82 (07) :1403-1413

[22] Ruthenium-Catalyzed Direct Arylations Through C-H Bond Cleavages [J].

Ackermann, Lutz ;

Vicente, Ruben .

C-H ACTIVATION, 2010, 292 :211-229

[23] Metal-catalyzed direct alkylations of (hetero)arenes via C-H bond cleavages with unactivated alkyl halides [J].

Ackermann, Lutz .

CHEMICAL COMMUNICATIONS, 2010, 46 (27) :4866-4877

[24] Palladium-Catalyzed Dehydrogenative Direct Arylations of 1,2,3-Triazoles [J].

Ackermann, Lutz ;

Jeyachandran, Rajkumar ;

Potukuchi, Harish K. ;

Novak, Petr ;

Buettner, Lea .

ORGANIC LETTERS, 2010, 12 (09) :2056-2059

[25] Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage [J].

Ackermann, Lutz ;

Vicente, Ruben ;

Kapdi, Anant R. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) :9792-9826

[26] Regioselective Ruthenium-Catalyzed Direct Benzylations of Arenes through C-H Bond Cleavages [J].

Ackermann, Lutz ;

Novak, Petr .

ORGANIC LETTERS, 2009, 11 (21) :4966-4969

[27] Catalytic Direct Arylations in Polyethylene Glycol (PEG): Recyclable Palladium(0) Catalyst for C-H Bond Cleavages in the Presence of Air [J].

Ackermann, Lutz ;

Vicente, Ruben .

ORGANIC LETTERS, 2009, 11 (21) :4922-4925

[28] Ruthenium-Catalyzed Direct Arylations of N-Aryl 1,2,3-Triazoles with Aryl Chlorides as Electrophiles [J].

Ackermann, Lutz ;

Born, Robert ;

Vicente, Ruben .

CHEMSUSCHEM, 2009, 2 (06) :546-549

[29] Ruthenium-Catalyzed Regioselective Direct Alkylation of Arenes with Unactivated Alkyl Halides through C-H Bond Cleavage [J].

Ackermann, Lutz ;

Novak, Petr ;

Vicente, Ruben ;

Hofmann, Nora .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (33) :6045-6048

[30]

Alvarez-Builla J, 2011, HETEROCYCLIC CHEM

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