Oxidative Cleavage of the Carbon-Carbon σ-Bond Using Reusable Copper on Iron

被引：35

作者：

Song, Ren-Jie ^{[1
,2
]}

Liu, Yu ^{[2
]}

Hu, Rui-Xiang ^{[2
]}

Liu, Yan-Yun ^{[2
]}

Wu, Ji-Cheng ^{[2
]}

Yang, Xu-Heng ^{[2
]}

Li, Jin-Heng ^{[1
]}

机构：

[1] Hunan Univ, Coll Chem & Chem Engn, Changsha 410082, Hunan, Peoples R China

[2] Hunan Normal Univ, Key Lab Chem Biol & Tradit Chinese Med Res, Minist Educ, Changsha 410081, Hunan, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2011年 / 353卷 / 09期

关键词：

alpha-aminocarbonyl compounds; copper; formylamides; iron; oxidative cleavage; reusable catalysts; C-C BONDS; BETA-METHYL ELIMINATION; SELECTIVE SYNTHESIS; RING-CLEAVAGE; R-CN; OXYGEN; POLYMERIZATION; DERIVATIVES; ACTIVATION; COMPLEXES;

D O I：

10.1002/adsc.201100225

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

An efficient and resuble copper on iron catalyst has been prepared for the cleavage of the carbon-carbon sigma-bond in alpha-aminocarbonyl compounds leading to the corresponding formylamides and acids with a maximal TON of up to 51,000. It is noteworthy that the copper on iron catalyst can be easily separated from the reaction mixture, and retains its activity after several reuses.

引用

页码：1467 / 1473

页数：7

共 70 条

[31] Ring opening in the hydrostannation of methylenecyclopropanes: Effect of the catalyst and substrate [J].

Lautens, M ;

Meyer, C ;

Lorenz, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (43) :10676-10677

[32] Reactivity of dioxygen-copper systems [J].

Lewis, EA ;

Tolman, WB .

CHEMICAL REVIEWS, 2004, 104 (02) :1047-1076

[33] Ruthenium-catalyzed regioselective 1,3-methylene transfer by cleavage of two adjacent σ-carbon-carbon bonds:: An easy and selective synthesis of highly subsituted benzenes [J].

Lian, JJ ;

Odedra, A ;

Wu, CJ ;

Liu, RS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (12) :4186-4187

[34]

Ma S., 2003, ANGEW CHEM, V115, P193

[35]

Ma SM, 2003, ANGEW CHEM INT EDIT, V42, P184

[36] Copper-catalyzed oxidation of amines with molecular oxygen [J].

Maeda, Y ;

Nishimura, T ;

Uemura, S .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2003, 76 (12) :2399-2403

[37] Palladium-Catalyzed Sequential Carbon-Carbon Bond Cleavage/Formation Producing Arylated Benzolactones [J].

Matsuda, Takanori ;

Shigeno, Masanori ;

Murakami, Masahiro .

ORGANIC LETTERS, 2008, 10 (22) :5219-5221

[38] Enantioselective C-C bond cleavage creating chiral quaternary carbon centers [J].

Matsuda, Takanori ;

Shigeno, Masanori ;

Makino, Masaomi ;

Murakami, Masahiro .

ORGANIC LETTERS, 2006, 8 (15) :3379-3381

[39] Palladium-catalyzed asymmetric arylation, vinylation, and allenylation of tert-cyclobutanois via enantioselective C-C bond cleavage [J].

Matsumura, S ;

Maeda, Y ;

Nishimura, T ;

Uemura, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (29) :8862-8869

[40] Iron-Mediated Cleavage of C-C Bonds in Vicinal Tricarbonyl Compounds in Water [J].

Mecinovic, Jasmin ;

Hamed, Refaat B. ;

Schofield, Christopher J. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (15) :2796-2800

← 1 2 3 4 5 6 7 →