Ruthenium-Catalyzed Oxidative C-H Bond Alkenylations in Water: Expedient Synthesis of Annulated Lactones

被引：292

作者：

Ackermann, Lutz ^{[1
]}

Pospech, Jola ^{[1
]}

机构：

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

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 16期

关键词：

DIRECT ARYLATIONS; ROOM-TEMPERATURE; BENZOIC-ACIDS; COUPLING REACTIONS; ARYL CHLORIDES; HECK REACTIONS; CARBON BONDS; FUNCTIONALIZATION; CLEAVAGE; ACTIVATION;

D O I：

10.1021/ol201563r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ruthenium-catalyzed cross-dehydrogenative C-H bond alkenylations occurred efficiently in environmentally benign water, which was exploited for an oxidative phthalide synthesis with ample scope. Mechanistic studies provided strong evidence for the oxidative alkenylation to proceed by an irreversible C-H bond metalation via acetate assistance.

引用

页码：4153 / 4155

页数：3

共 78 条

[1] Phosphine oxides as preligands in ruthenium-catalyzed arylations via C-H bond functionalization using aryl chlorides
Ackermann, L
[J]. ORGANIC LETTERS, 2005, 7 (14) : 3123 - 3125
[2] Dehydrative Direct Arylations of Arenes with Phenols via Ruthenium-Catalyzed C-H and C-OH Bond Functionalizations
Ackermann, Lutz
Mulzer, Michael
[J]. ORGANIC LETTERS, 2008, 10 (21) : 5043 - 5045
[3] Assisted ruthenium-catalyzed C-H bond activation: Carboxylic acids as cocatalysts for generally applicable direct arylations in apolar solvents
Ackermann, Lutz
Vicente, Ruben
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[J]. ORGANIC LETTERS, 2008, 10 (11) : 2299 - 2302
[4] 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
[5] Ruthenium-Catalyzed Direct C-H Bond Arylations of Heteroarenes
Ackermann, Lutz
Lygin, Alexander V.
[J]. ORGANIC LETTERS, 2011, 13 (13) : 3332 - 3335
[6] Ruthenium-Catalyzed Oxidative Synthesis of 2-Pyridones through C-H/N-H Bond Functionalizations
Ackermann, Lutz
Lygin, Alexander V.
Hofmann, Nora
[J]. ORGANIC LETTERS, 2011, 13 (12) : 3278 - 3281
[7] Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope
Ackermann, Lutz
[J]. CHEMICAL REVIEWS, 2011, 111 (03) : 1315 - 1345
[8] Carboxylate-Assisted Ruthenium-Catalyzed Direct Alkylations of Ketimines
Ackermann, Lutz
Hofmann, Nora
Vicente, Ruben
[J]. ORGANIC LETTERS, 2011, 13 (07) : 1875 - 1877
[9] Mechanistic Insight into Direct Arylations with Ruthenium(II) Carboxylate Catalysts
Ackermann, Lutz
Vicente, Ruben
Potukuchi, Harish K.
Pirovano, Valentina
[J]. ORGANIC LETTERS, 2010, 12 (21) : 5032 - 5035
[10] Regioselective syntheses of fully-substituted 1,2,3-triazoles: the CuAAC/C-H bond functionalization nexus
Ackermann, Lutz
Potukuchi, Harish Kumar
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (20) : 4503 - 4513

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