Enantioselective Di-/Perfluoroalkylation of β-Ketoesters Enabled by Cooperative Photoredox/Nickel Catalysis

被引:72
作者
Liu, Jing [1 ]
Ding, Wei [1 ]
Zhou, Quan-Quan [1 ]
Liu, Dan [1 ]
Lu, Liang-Qu [1 ]
Xiao, Wen-Jing [1 ,2 ]
机构
[1] Cent China Normal Univ, Coll Chem, Hubei Int Sci & Technol Cooperat Base Pesticide &, Key Lab Pesticide & Chem Biol,Minist Educ, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China
[2] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Gansu, Peoples R China
基金
中国国家自然科学基金;
关键词
TRANSFER RADICAL-ADDITION; ASYMMETRIC TRIFLUOROMETHYLATION; SELECTIVE DIFLUOROALKYLATION; ALPHA-TRIFLUOROMETHYLATION; MERGING PHOTOREDOX; LIGHT; FLUORINATION; ALKENES; ALDEHYDES; PERFLUOROALKYLATION;
D O I
10.1021/acs.orglett.7b03826
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Efficient and enantioselective radical difluoroalkylation and perfluoroalkylation reactions of beta-ketoesters were successfully developed through an asymmetric photoredox and nickel catalysis cascade. This protocol provides R-f-containing quaternary stereocenters in up to 67% yield and 95:5 er with ethyl iododifluoroacetate and perfluoroalkyl iodides (C3F7I and C4F9I) as radical sources under extremely mild conditions.
引用
收藏
页码:461 / 464
页数:4
相关论文
共 63 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] Oxydifluoromethylation of Alkenes by Photoredox Catalysis: Simple Synthesis of CF2H-Containing Alcohols
    Arai, Yusuke
    Tomita, Ren
    Ando, Gaku
    Koike, Takashi
    Akita, Munetaka
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (04) : 1262 - 1265
  • [3] Catalytic Enantioselective Synthesis of Highly Functionalized Difluoromethylated Cyclopropanes
    Bos, Maxence
    Huang, Wei-Sheng
    Poisson, Thomas
    Pannecoucke, Xavier
    Charette, Andre B.
    Jubault, Philippe
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (43) : 13319 - 13323
  • [4] Carbon-Carbon Bond-Forming Reductive Elimination from Isolated Nickel(III) Complexes
    Bour, James R.
    Camasso, Nicole M.
    Meucci, Elizabeth A.
    Kampf, Jeff W.
    Canty, Allan J.
    Sanford, Melanie S.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (49) : 16105 - 16111
  • [5] Enantioselective Catalysis of Photochemical Reactions
    Brimioulle, Richard
    Lenhart, Dominik
    Maturi, Mark M.
    Bach, Thorsten
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (13) : 3872 - 3890
  • [6] Inhibition of clinically relevant mutant variants of HIV-1 by quinazolinone non-nucleoside reverse transcriptase inhibitors
    Corbett, JW
    Ko, SS
    Rodgers, JD
    Gearhart, LA
    Magnus, NA
    Bacheler, LT
    Diamond, S
    Jeffrey, S
    Klabe, RM
    Cordova, BC
    Garber, S
    Logue, K
    Trainor, GL
    Anderson, PS
    Erickson-Viitanen, SK
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (10) : 2019 - 2030
  • [7] Highly Enantioselective Copper-Catalyzed Electrophilic Trifluoromethylation of β-Ketoesters
    Deng, Qing-Hai
    Wadepohl, Hubert
    Gade, Lutz H.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (26) : 10769 - 10772
  • [8] The Synthesis of a New Class of Chiral Pincer Ligands and Their Applications in Enantioselective Catalytic Fluorinations and the Nozaki-Hiyama-Kishi Reaction
    Deng, Qing-Hai
    Wadepohl, Hubert
    Gade, Lutz H.
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (52) : 14922 - 14928
  • [9] Bifunctional Photocatalysts for Enantioselective Aerobic Oxidation of β-Ketoesters
    Ding, Wei
    Lu, Liang-Qiu
    Quan-Quan Zhou
    Wei, Yi
    Chen, Jia-Rong
    Xiao, Wen-Jing
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (01) : 63 - 66
  • [10] Photocatalytic aerobic oxidation/semipinacol rearrangement sequence: a concise route to the core of pseudoindoxyl alkaloids
    Ding, Wei
    Zhou, Quan-Quan
    Xuan, Jun
    Li, Tian-Ren
    Lu, Liang-Qiu
    Xiao, Wen-Jing
    [J]. TETRAHEDRON LETTERS, 2014, 55 (33) : 4648 - 4652