K2S2O8-Mediated Dioxygenation of Aryl Alkenes Using N-Hydroxylamines and Air

被引：13

作者：

Bag, Raghunath ^{[1
]}

Punniyamurthy, Tharmalingam ^{[1
]}

机构：

[1] Indian Inst Technol Guwahati, Dept Chem, Gauhati 781039, India

来源：

CHEMISTRYSELECT | 2018年 / 3卷 / 22期

关键词：

Aerobic; aryl alkenes; dihydroxylation; N-hydroxylamines; one-pot; CATALYTIC ASYMMETRIC DIHYDROXYLATION; OLEFIN CIS-DIHYDROXYLATION; BETA-KETO SULFONES; ONE-POT SYNTHESIS; METAL-FREE; HYDROGEN-PEROXIDE; MOLECULAR-OXYGEN; VICINAL DIFUNCTIONALIZATION; AEROBIC DIOXYGENATION; CASCADE BIOCATALYSIS;

D O I：

10.1002/slct.201801154

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The vicinal dioxygenation of aryl alkenes is reported using N-hydroxylamines and air in the presence of potassium persulfate (K2S2O8). The alkene is first oxidized to beta-aminoxy alkyl hydroperoxide, which is insitu reduced to the diol using molybdenum hexacarbonyl [Mo(CO)(6)] and base. Metal-free, aerobic conditions and the substrate scope are the important practical features.

引用

页码：6152 / 6155

页数：4

共 74 条

[1] Vicinal Difunctionalization of Alkenes under Iodine(III) Catalysis involving Lewis Base Adducts [J].

Aertker, Kristina ;

Rama, Raquel J. ;

Opalach, Julita ;

Muniz, Kilian .

ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (08) :1290-1294

[2] Alkene anti-Dihydroxylation with Malonoyl Peroxides [J].

Alamillo-Ferrer, Carla ;

Davidson, Stuart C. ;

Rawling, Michael J. ;

Theodoulou, Natalie H. ;

Campbell, Matthew ;

Humphreys, Philip G. ;

Kennedy, Alan R. ;

Tomkinson, Nicholas C. O. .

ORGANIC LETTERS, 2015, 17 (20) :5132-5135

[3] Cross-dehydrogenative coupling of α-C(sp3)-H of ethers/alkanes with C(sp2)-H of heteroarenes under metal-free conditions [J].

Ambala, Srinivas ;

Thatikonda, Thanusha ;

Sharma, Shweta ;

Munagala, Gurunadham ;

Yempalla, Kushalava Reddy ;

Vishwakarma, Ram A. ;

Singh, Parvinder Pal .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (46) :11341-11350

[4] Enantioselective Allylic C-H Oxidation of Terminal Olefins to Isochromans by Palladium(II)/Chiral Sulfoxide Catalysis [J].

Ammann, Stephen E. ;

Liu, Wei ;

White, M. Christina .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (33) :9571-9575

[5] Copper(I)-Catalyzed Oxidation of Alkenes Using Molecular Oxygen and Hydroxylamines: Synthesis and Reactivity of α-Oxygenated Ketones [J].

Andia, Alexander A. ;

Miner, Matthew R. ;

Woerpel, K. A. .

ORGANIC LETTERS, 2015, 17 (11) :2704-2707

[6] Aerobic Metal-Free Dioxygenation of Alkenes with tert-Butyl Nitrite and N-Hydroxylamines [J].

Bag, Raghunath ;

Sar, Dinabandhu ;

Punniyamurthy, Tharmalingam .

ACS OMEGA, 2017, 2 (09) :6278-6290

[7] Recent Advances in Radical Dioxygenation of Olefins [J].

Bag, Raghunath ;

De, Pinaki Bhusan ;

Pradhan, Sourav ;

Punniyamurthy, Tharmalingam .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (37) :5424-5438

[8] Iron(III)-catalyzed aerobic dioxygenation of styrenes using N-hydroxyphthalimide and N-hydroxybenzotriazole [J].

Bag, Raghunath ;

Sar, Dinabandhu ;

Punniyamurthy, Tharmalingam .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (12) :3246-3255

[9] Copper(II)-Catalyzed Direct Dioxygenation of Alkenes with Air and N-Hydroxyphthalimide: Synthesis of β-Keto-N-alkoxyphthalimides [J].

Bag, Raghunath ;

Sar, Dinabandhu ;

Punniyamurthy, Tharmalingam .

ORGANIC LETTERS, 2015, 17 (08) :2010-2013

[10] Osmium-free direct syn-dihydroxylation of alkenes [J].

Bataille, Carole J. R. ;

Donohoe, Timothy J. .

CHEMICAL SOCIETY REVIEWS, 2011, 40 (01) :114-128

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