Manganese-Catalyzed Carbonylative Annulations for Redox-Neutral Late-Stage Diversification

被引：41

作者：

Liang, Yu-Feng ^{[1
]}

Steinbock, Ralf ^{[1
]}

Muench, Annika ^{[2
]}

Stalke, Dietmar ^{[2
]}

Ackermann, Lutz ^{[1
]}

机构：

[1] Georg August Univ Gottingen, Inst Organ & Biomol Chem, Tammannstr 2, D-37077 Gottingen, Germany

[2] Georg August Univ Gottingen, Inst Anorgan Chem, Tammannstr 2, D-37077 Gottingen, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2018年 / 57卷 / 19期

关键词：

annulation; carbonylation; late-stage modification; manganese; traceless directing groups; C-H ACTIVATION; BOND ACTIVATION; REGIOSELECTIVE CARBONYLATION; OXIDATIVE CARBONYLATION; ALIPHATIC-AMINES; C(SP(3))-H BONDS; INTERNAL ALKYNES; CARBON-MONOXIDE; BETA-LACTAMS; ANILINES;

D O I：

10.1002/anie.201801111

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An inexpensive, nontoxic manganese catalyst enabled unprecedented redox-neutral carbonylative annulations under ambient pressure. The manganese catalyst outperformed all other typically used base and precious-metal catalysts. The outstanding versatility of the manganese catalysis manifold was reflected by ample substrate scope, setting the stage for effective late-stage manipulations under racemization-free conditions of a wealth of marketed drugs and natural products, including alkaloids, amino acids, steroids, and carbohydrates.

引用

页码：5384 / 5388

页数：5

共 72 条

[21] Highly Regioselective Carbonylation of Unactivated C(sp3)-H Bonds by Ruthenium Carbonyl [J].

Hasegawa, Nao ;

Charra, Valentine ;

Inoue, Satoshi ;

Fukumoto, Yoshiya ;

Chatani, Naoto .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (21) :8070-8073

[22] Manganese- Catalyzed Dehydrogenative [4+2] Annulation of N-H Imines and Alkynes by C- H/N- H Activation** [J].

He, Ruoyu ;

Huang, Zhi-Tang ;

Zheng, Qi-Yu ;

Wang, Congyang .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (19) :4950-4953

[23] Ruthenium-Catalyzed Carbonylation at Ortho C-H Bonds in Aromatic Amides Leading to Phthalimides: C-H Bond Activation Utilizing a Bidentate System [J].

Inoue, Satoshi ;

Shiota, Hirotaka ;

Fukumoto, Yoshiya ;

Chatani, Naoto .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (20) :6898-+

[24] Pyrido[1,2-a]pyrimidin-4-one derivatives as a novel class of selective aldose reductase inhibitors exhibiting antioxidant activity [J].

La Motta, Concettina ;

Sartini, Stefania ;

Mugnaini, Laura ;

Simorini, Francesca ;

Taliani, Sabrina ;

Salerno, Silvia ;

Marini, Anna Maria ;

Da Settimo, Federico ;

Lavecchia, Antonio ;

Novellino, Ettore ;

Cantore, Miriam ;

Failli, Paola ;

Ciuffi, Mario .

JOURNAL OF MEDICINAL CHEMISTRY, 2007, 50 (20) :4917-4927

[25]

Li W., 2015, ANGEW CHEM, V127, P1913

[26]

Li W., 2014, ANGEW CHEM, V126, P2475

[27] From Anilines to Isatins: Oxidative Palladium-Catalyzed Double Carbonylation of C-H Bonds [J].

Li, Wu ;

Duan, Zhengli ;

Zhang, Xueye ;

Zhang, Heng ;

Wang, Mengfan ;

Jiang, Ru ;

Zeng, Hongyao ;

Liu, Chao ;

Lei, Aiwen .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (06) :1893-1896

[28] Palladium-Catalyzed Oxidative Carbonylation of N-Allylamines for the Synthesis of β-Lactams [J].

Li, Wu ;

Liu, Chao ;

Zhang, Heng ;

Ye, Keyin ;

Zhang, Guanghui ;

Zhang, Wangzheng ;

Duan, Zhengli ;

You, Shuli ;

Lei, Aiwen .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (09) :2443-2446

[29] Rh-catalyzed aerobic oxidative cyclization of anilines, alkynes, and CO [J].

Li, Xinyao ;

Pan, Jun ;

Wu, Hao ;

Jiao, Ning .

CHEMICAL SCIENCE, 2017, 8 (09) :6266-6273

[30] Rh-Catalyzed Construction of Quinolin-2(1H)-ones via C-H Bond Activation of Simple Anilines with CO and Alkynes [J].

Li, Xinyao ;

Li, Xinwei ;

Jiao, Ning .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (29) :9246-9249

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