Graphite oxide: a selective and highly efficient oxidant of thiols and sulfides

被引：223

作者：

Dreyer, Daniel R. ^{[1
]}

Jia, Hong-Peng ^{[1
]}

Todd, Alexander D. ^{[1
]}

Geng, Jianxin ^{[1
]}

Bielawski, Christopher W. ^{[1
]}

机构：

[1] Univ Texas Austin, Dept Chem & Biochem, Austin, TX 78712 USA

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2011年 / 9卷 / 21期

基金：

美国国家科学基金会;

关键词：

HETEROGENEOUS CATALYSIS; GRAPHENE OXIDE; HYDROGEN-PEROXIDE; OXIDATION; DISULFIDES; SULFOXIDES; OXYGEN; H2O2;

D O I：

10.1039/c1ob06102j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The selective oxidation of thiols to disulfides and sulfides to sulfoxides using graphite oxide (GO), a heterogeneous carbocatalyst obtained from low cost, commercial starting materials is described. The aforementioned oxidation reactions were found to proceed rapidly (as short as 10 min in some cases) and in good yield (51-100%) (19 examples). No over-oxidation of the substrates was observed, and GO's heterogeneous nature facilitated isolation and purification of the target products.

引用

页码：7292 / 7295

页数：4

共 32 条

[1] Toxicity of Graphene and Graphene Oxide Nanowalls Against Bacteria [J].

Akhavan, Omid ;

Ghaderi, Elham .

ACS NANO, 2010, 4 (10) :5731-5736

[2] Selective aerobic oxidation of sulfides using a novel palladium complex as the catalyst precursor [J].

Aldea, R ;

Alper, H .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (26) :8365-8366

[3]

Backvall J.-E., 2011, Modern Oxidation Methods, V2nd

[4] Aerobic oxidation of thiols to disulfides using iron metal-organic frameworks as solid redox catalysts [J].

Dhakshinamoorthy, Amarajothi ;

Alvaro, Mercedes ;

Garcia, Hermenegildo .

CHEMICAL COMMUNICATIONS, 2010, 46 (35) :6476-6478

[5] The chemistry of graphene oxide [J].

Dreyer, Daniel R. ;

Park, Sungjin ;

Bielawski, Christopher W. ;

Ruoff, Rodney S. .

CHEMICAL SOCIETY REVIEWS, 2010, 39 (01) :228-240

[6] Carbocatalysis: Heterogeneous carbons finding utility in synthetic chemistry [J].

Dreyer, Daniel R. ;

Bielawski, Christopher W. .

CHEMICAL SCIENCE, 2011, 2 (07) :1233-1240

[7] Reduction of graphite oxide using alcohols [J].

Dreyer, Daniel R. ;

Murali, Shanthi ;

Zhu, Yanwu ;

Ruoff, Rodney S. ;

Bielawski, Christopher W. .

JOURNAL OF MATERIALS CHEMISTRY, 2011, 21 (10) :3443-3447

[8] From Conception to Realization: An Historial Account of Graphene and Some Perspectives for Its Future [J].

Dreyer, Daniel R. ;

Ruoff, Rodney S. ;

Bielawski, Christopher W. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (49) :9336-9344

[9] Graphene Oxide: A Convenient Carbocatalyst for Facilitating Oxidation and Hydration Reactions [J].

Dreyer, Daniel R. ;

Jia, Hong-Peng ;

Bielawski, Christopher W. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (38) :6813-6816

[10] Fe(salan)-catalyzed asymmetric oxidation of sulfides with hydrogen peroxide in water [J].

Egami, Hiromichi ;

Katsuki, Tsutomu .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (29) :8940-+

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