Coupling Reaction between Aldehydes and Non-Activated Hydrocarbons via the Reductive Radical-Polar Crossover Pathway

被引：49
|
作者：
Yahata, Kenzo [1 ]
Sakurai, Shu [1 ]
Hori, Shuhei [1 ]
Yoshioka, Shin [1 ]
Kaneko, Yuki [1 ]
Hasegawa, Kai [1 ]
Akai, Shuji [1 ]
机构：
[1] Osaka Univ, Suita, Osaka, Japan
来源：
ORGANIC LETTERS | 2020年 / 22卷 / 03期
关键词：
C(SP(3))-H FUNCTIONALIZATION; CARBONYL-COMPOUNDS; DECATUNGSTATE; ALKYLATION; ALKENES; ACCESS; FLUORINATION; BENZYLATION; CARBANIONS; ALLYLATION;
D O I：
10.1021/acs.orglett.0c00096
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Herein, we describe the generation of an organochromium-type carbanion species from a non-activated C-H bond and its nucleophilic addition to aldehydes. The catalytic carbanion generation occurred through formal deprotonation of a non-activated C-H bond under mild conditions and did not need the prefunctionalization or anion stabilizing group. Carbon radical intermediates generated by decatungstate photocatalyst-mediated hydrogen abstraction were captured by a chromium salt with the reductive radical-polar crossover reaction to produce organochromium carbanions.
引用
收藏
页码：1199 / 1203
页数：5
相关论文
共 18 条
  • [1] Hydroarylation of Arenes via Reductive Radical-Polar Crossover
    Flynn, Autumn R.
    McDaniel, Kelly A.
    Hughes, Meredith E.
    Vogt, David B.
    Jui, Nathan T.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (20) : 9163 - 9168
  • [2] Dual Photoredox and Titanium Catalyzed Regioselective Allenylation of Aldehydes via Reductive Radical-Polar Crossover
    Xiao, Zulin
    Shang, Wenzhe
    Huang, Tao
    He, Lei
    Li, Jingyao
    Luo, Shen
    He, Xiaoxia
    Li, Xiang
    Li, Fusheng
    CHINESE JOURNAL OF CHEMISTRY, 2025, 43 (03) : 275 - 280
  • [3] Synthesis of the acutumine spirocycle via a radical-polar crossover reaction
    Li, Fang
    Castle, Steven L.
    ORGANIC LETTERS, 2007, 9 (20) : 4033 - 4036
  • [4] Electroreductive formylation of activated alcohols via radical-polar crossover
    Kang, Jungtaek
    Cho, Heyjin
    Kim, Hyunwoo
    CHEMICAL COMMUNICATIONS, 2023, 59 (38) : 5733 - 5736
  • [5] Photocatalytic Reductive Radical-Polar Crossover for a Base-Free Corey-Seebach Reaction
    Donabauer, Karsten
    Murugesan, Kathiravan
    Rozman, Ursa
    Crespi, Stefano
    Koenig, Burkhard
    CHEMISTRY-A EUROPEAN JOURNAL, 2020, 26 (57) : 12945 - 12950
  • [6] Reactivity of Superbasic Carbanions Generated via Reductive Radical-Polar Crossover in the Context of Photoredox Catalysis
    Grotjahn, Sascha
    Graf, Christina
    Zelenka, Jan
    Pattanaik, Aryaman
    Mueller, Lea
    Kutta, Roger Jan
    Rehbein, Julia
    Roithova, Jana
    Gschwind, Ruth M.
    Nuernberger, Patrick
    Koenig, Burkhard
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2024, 63 (18)
  • [7] Photoinduced Palladium-Catalyzed 1,2-Difunctionalization of Electron-Rich Olefins via a Reductive Radical-Polar Crossover Reaction
    Fang, Hao
    Empel, Claire
    Atodiresei, Iuliana
    Koenigs, Rene M.
    ACS CATALYSIS, 2023, 13 (09) : 6445 - 6451
  • [8] Et B-Mediated Radical-Polar Crossover Reaction for Single-Step Coupling of 0, Te-Acetal, α,β-Unsaturated Ketones, and Aldehydes/Ketones
    Kamimura, Daigo
    Urabe, Daisuke
    Nagatomo, Masanori
    Inoue, Masayuki
    ORGANIC LETTERS, 2013, 15 (19) : 5122 - 5125
  • [9] Construction of a 6/5/9-membered tricyclic structure of cladiellins via radical-polar crossover reaction
    Masanori Nagatomo
    Yuki Fujimoto
    Keisuke Masuda
    Masayuki Inoue
    The Journal of Antibiotics, 2019, 72 : 486 - 489
  • [10] Regio-, diastereo- and enantioselectivity in the photocatalytic generation of carbanions via hydrogen atom transfer and reductive radical-polar crossover
    Grotjahn, Sascha
    Mueller, Lea
    Pattanaik, Aryaman
    Falk, Alexander
    Barison, Giorgia
    Bauer, Jonathan O.
    Rehbein, Julia
    Gschwind, Ruth M.
    Koenig, Burkhard
    ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (20): : 5890 - 5900
12