Iron-catalyzed trifluoromethylation with concomitant C-C bond formation via 1,2-migration of an aryl group

被引：159

作者：

Egami, Hiromichi ^{[1
,2
]}

Shimizu, Ryo ^{[1
,3
]}

Usui, Yoshihiko ^{[1
,3
]}

Sodeoka, Mikiko ^{[1
,2
,3
,4
]}

机构：

[1] RIKEN, Synthet Organ Chem Lab, Wako, Saitama 3510198, Japan

[2] Japan Sci & Technol Agcy, ERATO, Sodeoka Live Cell Chem Project, Wako, Saitama 3510198, Japan

[3] Saitama Univ, Grad Sch Sci & Engn, Sakura Ku, Saitama 3388570, Japan

[4] RIKEN Ctr Sustainable Resource Sci, Wako, Saitama 3510198, Japan

来源：

CHEMICAL COMMUNICATIONS | 2013年 / 49卷 / 66期

关键词：

ELECTROPHILIC TRIFLUOROMETHYLATION; SEMIPINACOL REARRANGEMENT; TERMINAL ALKENES; FLUORINE; OXYTRIFLUOROMETHYLATION; EFFICIENT; HYDROTRIFLUOROMETHYLATION; CONSTRUCTION; PRODUCT;

D O I：

10.1039/c3cc43936d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Iron-catalyzed trifluoromethylation with concomitant 1,2-migration of an aryl group starting from diaryl allyl alcohol was achieved under mild conditions. This reaction system affords alpha-substituted-beta-trifluoromethyl carbonyl compounds in high efficiency. In the case of substrates bearing different aryl groups, selective migration was observed.

引用

页码：7346 / 7348

页数：3

共 52 条

[1] The Productive Merger of Iodonium Salts and Organocatalysis: A Non-photolytic Approach to the Enantioselective α-Trifluoromethylation of Aldehydes [J].

Allen, Anna E. ;

MacMillan, David W. C. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (14) :4986-+

[2] Recent Progress in Catalytic Aromatic Trifluoromethylation [J].

Amii, Hideki .

JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2011, 69 (07) :752-762

[3] The effect of ring substitution on the O-neophyl rearrangement of 1,1-diarylalkoxyl radicals.: A product and time-resolved kinetic study [J].

Antunes, CSA ;

Bietti, M ;

Ercolani, G ;

Lanzalunga, O ;

Salamone, M .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (10) :3884-3891

[4] Copper-Catalyzed Oxidative Trifluoromethylation of Terminal Alkenes Using Nucleophilic CF3SiMe3: Efficient C(sp3)-CF3 Bond Formation [J].

Chu, Lingling ;

Qing, Feng-Ling .

ORGANIC LETTERS, 2012, 14 (08) :2106-2109

[5] Concise synthesis of oxindole derivatives bearing a 3-trifluoroethyl group: Copper-catalyzed trifluoromethylation of acryloanilides [J].

Egami, Hiromichi ;

Shimizu, Ryo ;

Sodeoka, Mikiko .

JOURNAL OF FLUORINE CHEMISTRY, 2013, 152 :51-55

[6] Trifluoromethylation Reactions for the Synthesis of β-Trifluoromethylamines [J].

Egami, Hiromichi ;

Kawamura, Shintaro ;

Miyazaki, Ayako ;

Sodeoka, Mikiko .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (30) :7841-7844

[7] Alkene Trifluoromethylation Coupled with CC Bond Formation: Construction of Trifluoromethylated Carbocycles and Heterocycles [J].

Egami, Hiromichi ;

Shimizu, Ryo ;

Kawamura, Shintaro ;

Sodeoka, Mikiko .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (14) :4000-4003

[8] Oxytrifluoromethylation of multiple bonds using copper catalyst under mild conditions [J].

Egami, Hiromichi ;

Shimizu, Ryo ;

Sodeoka, Mikiko .

TETRAHEDRON LETTERS, 2012, 53 (41) :5503-5506

[9] Novel 10-I-3 hypervalent iodine-based compounds for electrophilic trifluoromethylation [J].

Eisenberger, P ;

Gischig, S ;

Togni, A .

CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (09) :2579-2586

[10] Copper-catalyzed olefinic trifluoromethylation of enamides at room temperature [J].

Feng, Chao ;

Loh, Teck-Peng .

CHEMICAL SCIENCE, 2012, 3 (12) :3458-3462

← 1 2 3 4 5 6 →