Metal-free visible-light-mediated aerobic oxidation of silanes to silanols

被引：24

作者：

Wang, Jing ^{[1
]}

Li, Bin ^{[1
]}

Liu, Li-Chuan ^{[1
]}

Jiang, Chenran ^{[1
]}

He, Tao ^{[1
]}

He, Wei ^{[1
]}

机构：

[1] Tsinghua Univ, Sch Pharmaceut Sci, Beijing 100084, Peoples R China

来源：

SCIENCE CHINA-CHEMISTRY | 2018年 / 61卷 / 12期

基金：

中国国家自然科学基金; 国家重点研发计划;

关键词：

metal-free; photoredox; aerobic oxidation; silanes; MERGING PHOTOREDOX CATALYSIS; DIRECTING GROUP; SINGLET OXYGEN; HYDROGEN; AROMATIZATION; ORGANOSILANES; ALKENYLATION; GENERATION; PRODUCT; OXIDANT;

D O I：

10.1007/s11426-018-9289-9

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Oxidation of silanes into silanols using water/air has attracted considerable attention. The known methods with no exception required a metal catalyst. Herein we report the first metal-free method: 2 mol% Rose Bengal as the catalyst, air (O-2) as the oxidant, water as the additive and under visible light irradiation. While this method produces various silanols in a simple, cost-effective, efficient (92%-99% yields) and scalable fashion, its reaction mechanism is very different than the reported ones associated with metal catalysis.

引用

页码：1594 / 1599

页数：6

共 69 条

[1] O-ATOM INSERTION INTO SI-H BONDS BY DIOXIRANES - A STEREOSPECIFIC AND DIRECT CONVERSION OF SILANES INTO SILANOLS [J].

ADAM, W ;

MELLO, R ;

CURCI, R .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1990, 29 (08) :890-891

[2]

Adam W., 1990, ANGEW CHEM, V102, P916

[3]

[Anonymous], 2012, ANGEW CHEM

[4]

Asao N., 2010, ANGEW CHEM, V122, P10291, DOI DOI 10.1002/ANIE.201005138

[5] Nanostructured Materials as Catalysts: Nanoporous-Gold-Catalyzed Oxidation of Organosilanes with Water [J].

Asao, Naoki ;

Ishikawa, Yoshifumi ;

Hatakeyama, Naoya ;

Menggenbateer ;

Yamamoto, Yoshinori ;

Chen, Mingwei ;

Zhang, Wei ;

Inoue, Akihisa .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (52) :10093-10095

[6] Oxidative de-aromatization of para-alkyl phenols into para-peroxyquinols and para-quinols mediated by oxone as a source of singlet oxygen [J].

Carreño, MC ;

González-López, M ;

Urbano, A .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (17) :2737-2741

[7]

Carreno MC, 2006, ANGEW CHEM, V113, P2803

[8] Singlet Oxygen Generation from [Bis(trifluoroacetoxy)iodo]benzene and Hydrogen Peroxide [J].

Catir, Mustafa ;

Kilic, Hamdullah ;

Nardello-Rataj, Veronique ;

Aubry, Jean-Marie ;

Kazaz, Cavit .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (12) :4560-4564

[9] PROCEDURES FOR THE PREPARATION OF SILANOLS [J].

CELLA, JA ;

CARPENTER, JC .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1994, 480 (1-2) :23-26

[10] Recent developments in the synthesis and structure of organosilanols [J].

Chandrasekhar, V ;

Boomishankar, R ;

Nagendran, S .

CHEMICAL REVIEWS, 2004, 104 (12) :5847-5910

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