Photoredox-catalyzed hydroxyfluoroalkylation of alkene with simple fluoroalkyl iodides

被引：13

作者：

Geng, Xiaoyu ^{[1
]}

Lin, Fengguirong ^{[1
]}

Wang, Xiaoyang ^{[1
]}

Jiao, Ning ^{[1
,2
]}

机构：

[1] Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, Xue Yuan Rd 38, Beijing 100191, Peoples R China

[2] East China Normal Univ, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China

来源：

JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY | 2018年 / 355卷

基金：

中国国家自然科学基金;

关键词：

Oxygenation; Dioxygen; Photoredox-catalysis; Alkenes; Hydroxyfluoroalkylation; Difunctionalization; HIGHLY EFFICIENT; MOLECULAR-OXYGEN; OLEFINS; OXYTRIFLUOROMETHYLATION; FLUORINE; TRIFLUOROMETHYLATION; DERIVATIVES; ALKYNES; ACCESS;

D O I：

10.1016/j.jphotochem.2017.09.031

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Hydroxyfluoroalkylation of simple alkenes is presented with readily available fluoroalkyl iodides by the virtue of photoredox catalysis in good efficiency and regioselectivity. This chemistry features mild condition, simple operation and good substrate scope. A variety of styrenes as well as non-activated aliphatic alkenes can be selectively transformed to beta-fluoroalkylated alcohols. Preliminary mechanistic studies indicated a radical process with fluoroalkyl radicals which were generated from rethictive quenching of photocatalytic circle. (C) 2017 Elsevier B.V. All rights reserved.

引用

页码：194 / 201

页数：8

共 69 条

[61] Manganese-Catalyzed Aerobic Oxytrifluoromethylation of Styrene Derivatives Using CF3SO2Na as the Trifluoromethyl Source
Yang, Yi
Liu, Yingle
Jiang, Yan
Zhang, Yu
Vicic, David A.
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (13) : 6639 - 6648
[62] NICKEL-CATALYZED REACTION OF IODODIFLUOROACETATES WITH ALKENES AND ZINC - A NOVEL AND PRACTICAL ROUTE TO ALPHA,ALPHA-DIFLUORO-FUNCTIONALIZED ESTERS AND ALPHA,ALPHA,OMEGA,OMEGA-TETRAFLUORO DIESTERS
YANG, ZY
BURTON, DJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (19) : 5144 - 5149
[63] Three-component Oxytrifluoromethylation of Alkenes: Highly Efficient and Regioselective Difunctionalization of C=C Bonds Mediated by Photoredox Catalysts
Yasu, Yusuke
Koike, Takashi
Akita, Munetaka
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (38) : 9567 - 9571
[64] Unique properties for self-assembly of head-to-head type 4,4′-dihydroxystyrene dimers bearing two fluoroalkyl end-groups
Yoshida, Masato
Iizuka, Mari
Okuno, Keita
Sawada, Hideo
[J]. JOURNAL OF FLUORINE CHEMISTRY, 2016, 184 : 82 - 88
[65] Photoredox Catalysis with Visible Light
Zeitler, Kirsten
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) : 9785 - 9789
[66] Synthesis of heterocycles via palladium π-olefin and π-alkyne chemistry
Zeni, G
Larock, RC
[J]. CHEMICAL REVIEWS, 2004, 104 (05) : 2285 - 2309
[67] Progress in fluoroalkylation of organic compounds via sulfinatodehalogenation initiation system
Zhang, Cheng-Pan
Chen, Qing-Yun
Guo, Yong
Xiao, Ji-Chang
Gu, Yu-Cheng
[J]. CHEMICAL SOCIETY REVIEWS, 2012, 41 (12) : 4536 - 4559
[68] Dioxygen Activation under Ambient Conditions: Cu-Catalyzed Oxidative Amidation-Diketonization of Terminal Alkynes Leading to α-Ketoamides
Zhang, Chun
Jiao, Ning
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (01) : 28 - +
[69] N-Tosyl-S-difluoromethyl-S-phenylsulfoximine: A New Difluoromethylation Reagent for S-, N-, and C-Nucleophiles
Zhang, Wei
Wang, Fei
Hu, Jinbo
[J]. ORGANIC LETTERS, 2009, 11 (10) : 2109 - 2112

← 1 2 3 4 5 6 7 →