Photoinduced Trifluoromethylation with CF3Br as a Trifluoromethyl Source: Synthesis of α-CF3-Substituted Ketones

被引：19

作者：

Ma, Ransong ^{[1
]}

Deng, Zhoubin ^{[1
]}

Wang, Ke-Hu ^{[1
]}

Wang, Junjiao ^{[1
]}

Huang, Danfeng ^{[1
]}

Su, Yingpeng ^{[1
]}

Hu, Yulai ^{[1
,3
]}

Lv, Xiaobo ^{[2
]}

机构：

[1] Northwest Normal Univ, Coll Chem & Chem Engn, Lanzhou 730070, Peoples R China

[2] Shanghai Sinofluoro Chem Co Ltd, Shanghai 201321, Peoples R China

[3] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

来源：

ACS OMEGA | 2022年 / 7卷 / 16期

基金：

中国国家自然科学基金;

关键词：

SILYL ENOL ETHERS; PET-OXIDATIVE CYCLIZATION; ALKENES; HYDROTRIFLUOROMETHYLATION; BROMOTRIFLUOROMETHANE; REAGENTS; ALKYNES; ARENES;

D O I：

10.1021/acsomega.2c01241

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient and novel photoinduced trifluoromethylation employing CF3Br as a trifluoromethyl source is described. With commercially accessible fac-Ir(III)(ppy)3 as the catalyst, radical trifluoromethylation between O-silyl enol ether and CF3Br occurs successfully. This method provides various alpha-CF3-substituted ketones with a broad substrate scope in good yields under mild reaction conditions.

引用

页码：14357 / 14362

页数：6

共 48 条

[1] Mechanistic studies on PET-oxidative cyclization of unsaturated silyl enol ethers:: dependence of the regioselectivity on alcohol addition and pressure effects
Ackermann, L
Heidbreder, A
Wurche, F
Klärner, FG
Mattay, J
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1999, (04): : 863 - 869
[2] New Visible-Light-Triggered Photocatalytic Trifluoromethylation Reactions of Carbon-Carbon Multiple Bonds and (Hetero)Aromatic Compounds
Barata-Vallejo, Sebastian
Postigo, Al
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2020, 26 (49) : 11065 - 11084
[3] Where Does the Fluorine Come From? A Review on the Challenges Associated with the Synthesis of Organofluorine Compounds
Caron, Stephane
[J]. ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2020, 24 (04) : 470 - 480
[4] Electrophilic Trifluoromethylation by Use of Hypervalent Iodine Reagents
Charpentier, Julie
Frueh, Natalja
Togni, Antonio
[J]. CHEMICAL REVIEWS, 2015, 115 (02) : 650 - 682
[5] Photoredox-Catalyzed Cascade Radical Cyclization of Ester Arylpropiolates with CF3SO2CI To Construct 3-Trifluoromethyl Coumarin Derivatives
Chen, Long
Wu, Lianlian
Duan, Weijie
Wang, Tao
Li, Letian
Zhang, Keke
Zhu, Jingmei
Peng, Zhi
Xiong, Fei
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (15) : 8607 - 8614
[6] Oxidative Trifluoromethylation and Trifluoromethylthiolation Reactions Using (Trifluoromethyl)trimethylsilane as a Nucleophilic CF3 Source
Chu, Lingling
Qing, Feng-Ling
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (05) : 1513 - 1522
[7] REACTIONS OF BROMOTRIFLUOROMETHANE WITH ACID-DERIVATIVES IN THE PRESENCE OF ZINC
FRANCESE, C
TORDEUX, M
WAKSELMAN, C
[J]. TETRAHEDRON LETTERS, 1988, 29 (09) : 1029 - 1030
[8] GROBE J, 1995, SYNLETT, P641
[9] CF3SO2X (X = Na, Cl) as reagents for trifluoromethylation, trifluoromethylsulfenyl-, -sulfinyl- and -sulfonylation. Part 1: Use of CF3SO2Na
Guyon, Helene
Chachignon, Helene
Cahard, Dominique
[J]. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2017, 13 : 2764 - 2799
[10] Stereoselective Photoredox-Catalyzed Chlorotrifluoromethylation of Alkynes: Synthesis of Tetrasubstituted Alkenes
Han, Hong Sik
Lee, Young Jin
Jung, Young-Sik
Han, Soo Bong
[J]. ORGANIC LETTERS, 2017, 19 (08) : 1962 - 1965

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