Generation of CF3-Containing Epoxides and Aziridines by Visible-Light-Driven Trifluoromethylation of Allylic Alcohols and Amines

被引：177

作者：

Kim, Eunjin ^{[1
]}

Choi, Sungkyu ^{[1
]}

Kim, Heejeong ^{[1
]}

Cho, Eun Jin ^{[1
]}

机构：

[1] Hanyang Univ, Dept Chem & Appl Chem, Ansan 426791, Kyeonggido, South Korea

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2013年 / 19卷 / 20期

基金：

新加坡国家研究基金会;

关键词：

epoxides; nucleophilic addition; radical reactions; trifluoromethylation; visible light; PALLADIUM-CATALYZED TRIFLUOROMETHYLATION; OXYTRIFLUOROMETHYLATION; PHOTOCATALYSIS; ALKENES; ACIDS; ARYL;

D O I：

10.1002/chem.201300564

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Radical reactions! Efficient methods for the generation of CF 3-containing epoxides and aziridines have been developed (see scheme). A variety of allylic alcohols and allylic amines were transformed into the corresponding epoxides and aziridines by using [Ru(bpy)3]Cl 2 (bpy=2,2′-bipyridine), CF3I, and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (or N,N,N′,N′- tetramethylethylenediamine, TMEDA) under visible-light irradiation. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：6209 / 6212

页数：4

共 43 条

[21] Enantioselective catalytic aziridinations and asymmetric nitrene insertions into CH bonds
Müller, P
Fruit, C
[J]. CHEMICAL REVIEWS, 2003, 103 (08) : 2905 - 2919
[22] Trifluoromethylation of arenes and heteroarenes by means of photoredox catalysis
Nagib, David A.
MacMillan, David W. C.
[J]. NATURE, 2011, 480 (7376) : 224 - 228
[23] Visible light photoredox catalysis: applications in organic synthesis
Narayanam, Jagan M. R.
Stephenson, Corey R. J.
[J]. CHEMICAL SOCIETY REVIEWS, 2011, 40 (01) : 102 - 113
[24] Intermolecular Atom Transfer Radical Addition to Olefins Mediated by Oxidative Quenching of Photoredox Catalysts
Nguyen, John D.
Tucker, Joseph W.
Konieczynska, Marlena D.
Stephenson, Corey R. J.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (12) : 4160 - 4163
[25] Nielsen L.P. C., 2006, AZIRIDINES EPOXIDES, P229
[26] Aromatic trifluoromethylation catalytic in copper
Oishi, Masahiro
Kondo, Hideaki
Amii, Hideki
[J]. CHEMICAL COMMUNICATIONS, 2009, (14) : 1909 - 1911
[27] Padwa A, 2006, ARKIVOC, P6
[28] Photocatalysis by Phenothiazine Dyes: Visible-Light-Driven Oxidative Coupling of Primary Amines at Ambient Temperature
Park, Ji Hoon
Ko, Kyoung Chul
Kim, Eunchul
Park, Nojin
Ko, Ju Hong
Ryu, Do Hyun
Ahn, Tae Kyu
Lee, Jin Yong
Son, Seung Uk
[J]. ORGANIC LETTERS, 2012, 14 (21) : 5502 - 5505
[29] Iron(II)-Catalyzed Trifluoromethylation of Potassium Vinyltrifluoroborates
Parsons, Andrew T.
Senecal, Todd D.
Buchwald, Stephen L.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (12) : 2947 - 2950
[30] Photoredox catalyzed C-P bond forming reactions-visible light mediated oxidative phosphonylations of amines
Rueping, Magnus
Zhu, Shaoqun
Koenigs, Rene M.
[J]. CHEMICAL COMMUNICATIONS, 2011, 47 (30) : 8679 - 8681

← 1 2 3 4 5 →