Hydroxyl-Directed Ruthenium-Catalyzed C-H Bond Functionalization: Versatile Access to Fluorescent Pyrans

被引：151

作者：

Thirunavukkarasu, Vedhagiri S. ^{[1
]}

Donati, Margherita ^{[1
]}

Ackermann, Lutz ^{[1
]}

机构：

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

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 13期

关键词：

DIRECT ARYLATIONS; REGIOSELECTIVE SYNTHESIS; OXIDATIVE CYCLIZATION; EXPEDIENT SYNTHESIS; PALLADIUM; ACTIVATION; CLEAVAGE; ALKYNES; CONSTRUCTION; CARBOXYLATE;

D O I：

10.1021/ol301387t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Hydroxyl-assisted oxidative annulations of alkynes were accomplished with an inexpensive ruthenium(II) complex, delivering fluorescent pyrans via highly site selective as well as chemo- and regioselective C-H/O-H bond functionalizations.

引用

页码：3416 / 3419

页数：4

共 73 条

[41] Multiple arylation of phenols around the oxygen under palladium catalysis [J].

Kawamura, Y ;

Satoh, T ;

Miura, M ;

Nomura, M .

CHEMISTRY LETTERS, 1999, (09) :961-962

[42] Chelate-Assisted Oxidative Coupling Reaction of Arylamides and Unactivated Alkenes: Mechanistic Evidence for Vinyl C-H Bond Activation Promoted by an Electrophilic Ruthenium Hydride Catalyst [J].

Kwon, Ki-Hyeok ;

Lee, Do W. ;

Yi, Chae S. .

ORGANOMETALLICS, 2010, 29 (22) :5748-5750

[43] Dehydrative C-H Alkylation and Alkenylation of Phenols with Alcohols: Expedient Synthesis for Substituted Phenols and Benzofurans [J].

Lee, Dong-Hwan ;

Kwon, Ki-Hyeok ;

Yi, Chae S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (17) :7325-7328

[44] Preagostic Rh-H interactions and C-H bond functionalization: A combined experimental and theoretical investigation of rhodium(I) phosphinite complexes [J].

Lewis, JC ;

Wu, J ;

Bergman, RG ;

Ellman, JA .

ORGANOMETALLICS, 2005, 24 (23) :5737-5746

[45] Ruthenium-Catalyzed Oxidative C-H Bond Olefination of N-Methoxybenzamides Using an Oxidizing Directing Group [J].

Li, Bin ;

Ma, Jianfeng ;

Wang, Nuancheng ;

Feng, Huiliang ;

Xu, Shansheng ;

Wang, Baiquan .

ORGANIC LETTERS, 2012, 14 (03) :736-739

[46] Hydroxyl-directed C-H carbonylation enabled by mono-N-protected amino acid ligands: An expedient route to 1-isochromanones [J].

Lu, Yi ;

Leow, Dasheng ;

Wang, Xisheng ;

Engle, Keary M. ;

Yu, Jin-Quan .

CHEMICAL SCIENCE, 2011, 2 (05) :967-971

[47] Recent developments in natural product synthesis using metal-catalysed C-H bond functionalisation [J].

McMurray, Lindsay ;

O'Hara, Fionn ;

Gaunt, Matthew J. .

CHEMICAL SOCIETY REVIEWS, 2011, 40 (04) :1885-1898

[48] Synthesis of Naphtho[1,8-bc]pyran Derivatives and Related Compounds through Hydroxy Group Directed C-H Bond Cleavage under Rhodium Catalysis [J].

Mochida, Satoshi ;

Shimizu, Masaki ;

Hirano, Koji ;

Satoh, Tetsuya ;

Miura, Masahiro .

CHEMISTRY-AN ASIAN JOURNAL, 2010, 5 (04) :847-851

[49] Synthesis of Isochromene and Related Derivatives by Rhodium-Catalyzed Oxidative Coupling of Benzyl and Allyl Alcohols with Alkynes [J].

Morimoto, Keisuke ;

Hirano, Koji ;

Satoh, Tetsuya ;

Miura, Masahiro .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (22) :9548-9551

[50] Regioselective Synthesis of Indenols by Rhodium-Catalyzed C-H Activation and Carbocyclization of Aryl Ketones and Alkynes [J].

Muralirajan, Krishnamoorthy ;

Parthasarathy, Kanniyappan ;

Cheng, Chien-Hong .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (18) :4169-4172

← 1 2 3 4 5 6 7 8 →