Catalytic Asymmetric Hydrogen Atom Transfer Based on a Chiral Hydrogen Atom Donor Generated from TBADT and Chiral BINOL

被引：1
|
作者：
Li, Ling [1 ,2 ]
Zhang, Shi-qi [1 ]
Cui, Xin [1 ]
Zhao, Gang [2 ]
Tang, Zhuo [1 ]
Li, Guang-xun [1 ]
机构：
[1] Chinese Acad Sci, Chengdu Inst Biol, Chengdu 610041, Sichuan, Peoples R China
[2] Sichuan Univ, Coll Chem Engn, Chengdu 610065, Sichuan, Peoples R China
来源：
ORGANIC LETTERS | 2024年 / 26卷 / 39期
关键词：
FREE-RADICAL REDUCTIONS; ENANTIOSELECTIVE SYNTHESIS; DECATUNGSTATE ANION; PHOTOCATALYSIS; ACTIVATION; ALKANES; FUNCTIONALIZATION; HYDROSILYLATION; HYDROCARBONS; ALKYLATION;
D O I：
10.1021/acs.orglett.4c03175
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Enantioselective radical reactions mediated by TBADT have seldom been seen due to the inherent challenges. Herein, we disclose a new chiral hydrogen atom transfer (HAT) reagent that was generated easily from 8H-BINOL, potassium carbonate, and TBADT under irradiation. The new complex 8H-BINOL/DTs could be used as a chiral H donor. A series of azaarenes could be converted into the corresponding chiral compounds via radical addition followed by enantioselective HAT.
引用
收藏
页码：8371 / 8376
页数：6
相关论文
共 50 条
  • [31] O-H hydrogen bonding promotes H-atom transfer from α C-H bonds for C-alkylation of alcohols
    Jeffrey, Jenna L.
    Terrett, Jack A.
    MacMillan, David W. C.
    SCIENCE, 2015, 349 (6255) : 1532 - 1536
  • [32] Anthraquinone-based covalent organic framework as a recyclable direct hydrogen atom transfer photocatalyst for C-H functionalization
    Wang, Zitong
    Yeary, Pierce
    Fan, Yingjie
    Lin, Wenbin
    CHEMICAL SCIENCE, 2024, 15 (13) : 4920 - 4925
  • [33] Visible-Light-Induced Hydrogen Atom Transfer En Route to Exocylic Alkenylation of Cyclic Ethers Enabled by Electron Donor-Acceptor Complex
    Mandal, Tanumoy
    Das, Sanju
    Maji, Rohan
    De Sarkar, Suman
    ORGANIC LETTERS, 2023, 25 (42) : 7727 - 7732
  • [34] Alkene difunctionalization enabled by photocatalytic hydrogen atom transfer from haloalkane a-C(sp3)-H bonds
    Hao, Tonggang
    Shen, Jiahao
    Wei, Yin
    Shi, Min
    CHEM CATALYSIS, 2023, 3 (12):
  • [35] Photoinduced Copper-Catalyzed Asymmetric C(sp3)-H Alkynylation of Cyclic Amines by Intramolecular 1,5-Hydrogen Atom Transfer
    Guo, Rui
    Xiao, Haijing
    Li, Sijia
    Luo, Yixin
    Bai, Jiahui
    Zhang, Mengzhen
    Guo, Yinlong
    Qi, Xiaotian
    Zhang, Guozhu
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (34)
  • [36] Acid-promoted hydride transfer from an NADH analogue to a Cr(III)-superoxo complex via a proton-coupled hydrogen atom transfer
    Devi, Tarali
    Lee, Yong-Min
    Fukuzumi, Shunichi
    Nam, Wonwoo
    DALTON TRANSACTIONS, 2021, 50 (02) : 675 - 680
  • [37] Release of Formic Acid from Copper Formate: Hydride, Proton-Coupled Electron and Hydrogen Atom Transfer All Play their Role
    Pascher, Tobias F.
    Oncak, Milan
    van der Linde, Christian
    Beyer, Martin K.
    CHEMPHYSCHEM, 2019, 20 (11) : 1420 - 1424
  • [38] Triarylamine-based porous coordination polymers performing both hydrogen atom transfer and photoredox catalysis for regioselective α-amino C(sp3)-H arylation
    Li, Hanning
    Yang, Yang
    Jing, Xu
    He, Cheng
    Duan, Chunying
    CHEMICAL SCIENCE, 2021, 12 (24) : 8512 - 8520
  • [39] Enhancing Reactivity and Site-Selectivity in Hydrogen Atom Transfer from Amino Acid C-H Bonds via Deprotonation
    Pipitone, Luca Maria
    Carboni, Giulia
    Sorrentino, Daniela
    Galeotti, Marco
    Salamone, Michela
    Bietti, Massimo
    ORGANIC LETTERS, 2018, 20 (03) : 808 - 811
  • [40] Chiral Pt(II)/Pd(II) pincer complexes that show C-H•••Cl hydrogen bonding:: Synthesis and applications to catalytic asymmetric aldol and silylcyanation reactions
    Yoon, Myeong Sik
    Ramesh, Rengan
    Kim, Jeongryul
    Ryu, Dowook
    Ahn, Kyo Han
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2006, 691 (26) : 5927 - 5934
12345