Convenient Method for the Production of Deuterium Gas Catalyzed by an Iridium Complex and Its Application to the Deuteration of Organic Compounds

被引：9

作者：

Enomoto, Akane ^{[1
]}

Kajita, Shunpei ^{[1
]}

Fujita, Ken-ichi ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Human & Environm Studies, Sakyo Ku, Kyoto 6068501, Japan

来源：

CHEMISTRY LETTERS | 2019年 / 48卷 / 02期

关键词：

Deuterium; Deuteration; Iridium; PLATINUM-GROUP METAL; C-H ACTIVATION; DEGRADATION METHOD; PD/C-ET3N SYSTEM; AMBIENT-PRESSURE; EXCHANGE; HYDROGEN; MILD; GENERATION; SOLVENTS;

D O I：

10.1246/cl.180870

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new protocol for the production of deuterium gas from easily-obtainable deuterated methanol and deuterium oxide has been developed. The reaction of deuterated methanol and deuterium oxide in the presence of an iridium catalyst bearing a functional bipyridonate ligand and sodium hydroxide under reflux for 48 hours gave deuterium gas in 63% yield. Deuteration reactions of unsaturated compounds and bromosubstituted aromatic compounds using the generated deuterium gas in the presence of palladium/charcoal catalyst were also investigated.

引用

页码：106 / 109

页数：4

共 37 条

[1] 185-NM PHOTOCHEMISTRY OF BICYCLO[2.1.0]PENTANE AND CYCLOPENTENE [J].

ADAM, W ;

OPPENLANDER, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (13) :3924-3928

[2] One-step exchange-labelling of pyridines and other N-heteroaromatics using deuterium gas:: catalysis by heterogeneous rhodium and ruthenium catalysts [J].

Alexakis, Efstathios ;

Jones, John R. ;

Lockley, William J. S. .

TETRAHEDRON LETTERS, 2006, 47 (29) :5025-5028

[3] Deuterium- and Tritium-Labelled Compounds: Applications in the Life Sciences [J].

Atzrodt, Jens ;

Derdau, Volker ;

Kerr, William J. ;

Reid, Marc .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (07) :1758-1784

[4] Synthesis of β3 adrenergic receptor agonist LY377604 and its metabolite 4-hydroxycarbazole, labeled with carbon-14 and deuterium [J].

Czeskis, BA ;

Wheeler, WJ .

JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2005, 48 (06) :407-419

[5] Hydrogen Production from a Methanol-Water Solution Catalyzed by an Anionic Iridium Complex Bearing a Functional Bipyridonate Ligand under Weakly Basic Conditions [J].

Fujita, Ken-ichi ;

Kawahara, Ryoko ;

Aikawa, Takuya ;

Yamaguchi, Ryohei .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (31) :9057-9060

[6] NMR Chemical Shifts of Trace Impurities: Common Laboratory Solvents, Organics, and Gases in Deuterated Solvents Relevant to the Organometallic Chemist [J].

Fulmer, Gregory R. ;

Miller, Alexander J. M. ;

Sherden, Nathaniel H. ;

Gottlieb, Hugo E. ;

Nudelman, Abraham ;

Stoltz, Brian M. ;

Bercaw, John E. ;

Goldberg, Karen I. .

ORGANOMETALLICS, 2010, 29 (09) :2176-2179

[7] Syntheses of stable isotope-labeled 6β-hydroxycortisol, 6β-hydroxycortisone, and 6β-hydroxytestosterone [J].

Furuta, T ;

Suzuki, A ;

Matsuzawa, M ;

Shibasaki, H ;

Kasuya, Y .

STEROIDS, 2003, 68 (7-8) :693-703

[8] Using Deuterium in Drug Discovery: Leaving the Label in the Drug [J].

Gant, Thomas G. .

JOURNAL OF MEDICINAL CHEMISTRY, 2014, 57 (09) :3595-3611

[9] Kinetic Isotope Effects in the Study of Organometallic Reaction Mechanisms [J].

Gomez-Gallego, Mar ;

Sierra, Miguel A. .

CHEMICAL REVIEWS, 2011, 111 (08) :4857-4963

[10] NMR chemical shifts of common laboratory solvents as trace impurities [J].

Gottlieb, HE ;

Kotlyar, V ;

Nudelman, A .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (21) :7512-7515

← 1 2 3 4 →