Radical aminooxygenation of alkenes with N-fluoro-benzenesulfonimide (NFSI) and TEMPONa

被引：72

作者：

Li, Yi ^{[1
]}

Hartmann, Marcel ^{[1
]}

Daniliuc, Constantin Gabriel ^{[1
]}

Studer, Armido ^{[1
]}

机构：

[1] Univ Munster, Inst Organ Chem, D-48149 Munster, Germany

来源：

CHEMICAL COMMUNICATIONS | 2015年 / 51卷 / 26期

关键词：

CATALYZED INTERMOLECULAR AMINOACETOXYLATION; TRANSFER HYDROAMINATION; NITROGEN RADICALS; CENTERED RADICALS; OLEFINS; CYCLIZATIONS; GENERATION; FLUOROBENZENESULFONIMIDE; AMINOPALLADATION; CONSTRUCTION;

D O I：

10.1039/c5cc00591d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Reaction of various alkenes with commercially available N-fluorobenzenesulfonimide (NFSI) and TEMPONa provides the corresponding aminooxygenation products inmoderate to good yields. Single electron transfer from readily generated TEMPONa to NFSI allows for clean generation of the corresponding bissulfonylamidyl radical along with TEMPO. N-radical addition to an alkene and subsequent TEMPO trapping provides the corresponding aminooxygenation product.

引用

收藏

页码：5706 / 5709

页数：4

相关论文

共 55 条

[1] Palladium-catalyzed ring-forming aminoacetoxylation of alkenes [J].

Alexanian, EJ ;

Lee, C ;

Sorensen, EJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (21) :7690-7691

[2] Pd-Catalyzed Aryl C-H Imidation with Arene as the Limiting Reagent [J].

Boursalian, Gregory B. ;

Ngai, Ming-Yu ;

Hojczyk, Katarzyna N. ;

Ritter, Tobias .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (36) :13278-13281

[3]

Chatgilialoglu C., 2012, Encyclopedia of Radicals in Chemistry Biology and Materials, V1

[4] Radical-Transfer Hydroamination of Olefins with N-Aminated Dihydropyridines [J].

Chou, Chih-Ming ;

Guin, Joyram ;

Mueck-Lichtenfeld, Christian ;

Grimme, Stefan ;

Studer, Armido .

CHEMISTRY-AN ASIAN JOURNAL, 2011, 6 (05) :1197-1209

[5] ADDITIONS OF MALONONITRILE RADICALS TO ALKENES - NEW EXAMPLES OF 1,2-ASYMMETRIC INDUCTION IN IODINE AND PHENYLSELENIUM TRANSFER-REACTIONS [J].

CURRAN, DP ;

THOMA, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (11) :4436-4437

[6] Flexible Gold-Catalyzed Regioselective Oxidative Difunctionalization of Unactivated Alkenes [J].

de Haro, Teresa ;

Nevado, Cristina .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (04) :906-910

[7] Construction of tetrahydrofurans by PdII/PdIV-catalyzed aminooxygenation of alkenes [J].

Desai, Lopa V. ;

Sanford, Melanie S. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (30) :5737-5740

[8] Radical Addition of Arylboronic Acids to Various Olefins under Oxidative Conditions [J].

Dickschat, Arne ;

Studer, Armido .

ORGANIC LETTERS, 2010, 12 (18) :3972-3974

[9]

DIFFERDING E, 1991, SYNLETT, P187

[10] THE GENERATION OF NITROGEN RADICALS AND THEIR CYCLIZATIONS FOR THE CONSTRUCTION OF THE PYRROLIDINE NUCLEUS [J].

ESKER, JL ;

NEWCOMB, M .

ADVANCES IN HETEROCYCLIC CHEMISTRY, VOL 58, 1993, 58 :1-45

← 1 2 3 4 5 6 →