Ruthenium(II)-catalyzed cross-dehydrogenative C-H alkenylations by triazole assistance

被引：47

作者：

Tirler, Carina ^{[1
]}

Ackermann, Lutz ^{[1
]}

机构：

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

来源：

TETRAHEDRON | 2015年 / 71卷 / 26-27期

基金：

欧洲研究理事会;

关键词：

C-H activation; Mechanism; Olefination; Ruthenium; Triazoles; CATALYZED DIRECT ARYLATIONS; BOND ACTIVATION; CLICK CHEMISTRY; 1,3-DIPOLAR CYCLOADDITIONS; CONJUGATE ADDITION; TERMINAL ALKYNES; FUNCTIONALIZATION; METAL; 1,2,3-TRIAZOLES; CARBOXYLATE;

D O I：

10.1016/j.tet.2015.02.033

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ruthenium(II) carboxylate complexes allowed for efficient cross-dehydrogenative alkenylations of N-aryl-1,2,3-triazoles. The twofold C-H functionalizations occurred with excellent chemo-, regio-, site- and diastereoselectivities, and ample substrate scope. The versatile ruthenium(II) catalyst proved tolerant of moisture, air, and various electrophilic functional groups. Mechanistic studies were in good agreement with an initial C-H metalation by a cationic ruthenium(II) carboxylate, along with a subsequent migratory insertion of the olefin. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：4543 / 4551

页数：9

共 89 条

[1] Copper-catalyzed "click" reaction/direct arylation sequence: Modular syntheses of 1,2,3-triazoles
Ackermann, Lutz
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[2] Assisted ruthenium-catalyzed C-H bond activation: Carboxylic acids as cocatalysts for generally applicable direct arylations in apolar solvents
Ackermann, Lutz
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[5] Well-Defined Ruthenium(II) Carboxylate as Catalyst for Direct C-H/C-O Bond Arylations with Phenols in Water
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[J]. ORGANIC LETTERS, 2012, 14 (08) : 2146 - 2149
[6] Cationic Ruthenium(II) Catalysts for Oxidative C-H/N-H Bond Functionalizations of Anilines with Removable Directing Group: Synthesis of Indoles in Water
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[J]. ORGANIC LETTERS, 2012, 14 (03) : 764 - 767
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[8] Ruthenium-Catalyzed Oxidative C-H Bond Alkenylations in Water: Expedient Synthesis of Annulated Lactones
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[J]. ORGANIC LETTERS, 2011, 13 (16) : 4153 - 4155
[9] Ruthenium-Catalyzed Oxidative Annulation by Cleavage of C-H/N-H Bonds
Ackermann, Lutz
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[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (28) : 6379 - 6382
[10] Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope
Ackermann, Lutz
[J]. CHEMICAL REVIEWS, 2011, 111 (03) : 1315 - 1345

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