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

被引：157

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
Allen, Anna E.
MacMillan, David W. C.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (14) : 4986 - +
[2] Recent Progress in Catalytic Aromatic Trifluoromethylation
Amii, Hideki
[J]. 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
Antunes, CSA
Bietti, M
Ercolani, G
Lanzalunga, O
Salamone, M
[J]. 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
Chu, Lingling
Qing, Feng-Ling
[J]. ORGANIC LETTERS, 2012, 14 (08) : 2106 - 2109
[5] Concise synthesis of oxindole derivatives bearing a 3-trifluoroethyl group: Copper-catalyzed trifluoromethylation of acryloanilides
Egami, Hiromichi
Shimizu, Ryo
Sodeoka, Mikiko
[J]. JOURNAL OF FLUORINE CHEMISTRY, 2013, 152 : 51 - 55
[6] Trifluoromethylation Reactions for the Synthesis of β-Trifluoromethylamines
Egami, Hiromichi
Kawamura, Shintaro
Miyazaki, Ayako
Sodeoka, Mikiko
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (30) : 7841 - 7844
[7] Alkene Trifluoromethylation Coupled with CC Bond Formation: Construction of Trifluoromethylated Carbocycles and Heterocycles
Egami, Hiromichi
Shimizu, Ryo
Kawamura, Shintaro
Sodeoka, Mikiko
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (14) : 4000 - 4003
[8] Oxytrifluoromethylation of multiple bonds using copper catalyst under mild conditions
Egami, Hiromichi
Shimizu, Ryo
Sodeoka, Mikiko
[J]. TETRAHEDRON LETTERS, 2012, 53 (41) : 5503 - 5506
[9] Novel 10-I-3 hypervalent iodine-based compounds for electrophilic trifluoromethylation
Eisenberger, P
Gischig, S
Togni, A
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (09) : 2579 - 2586
[10] Copper-catalyzed olefinic trifluoromethylation of enamides at room temperature
Feng, Chao
Loh, Teck-Peng
[J]. CHEMICAL SCIENCE, 2012, 3 (12) : 3458 - 3462

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