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
  • [41] Evaluation of excited state bond weakening for ammonia synthesis from a manganese nitride: stepwise proton coupled electron transfer is preferred over hydrogen atom transfer
    Loose, Florian
    Wang, Dian
    Tian, Lei
    Scholes, Gregory D.
    Knowles, Robert R.
    Chirik, Paul J.
    CHEMICAL COMMUNICATIONS, 2019, 55 (39) : 5595 - 5598
  • [42] Synthesis of a calixarene-based chiral phase-transfer catalyst derived from cinchonine and its application in asymmetric alkylation
    Huang, Li
    Jin, Can
    Su, Weike
    JOURNAL OF CHEMICAL RESEARCH, 2012, (09) : 532 - 535
  • [43] Activation and Deactivation of Benzylic C-H Bonds Guided by Stereoelectronic Effects in Hydrogen Atom Transfer from Amides and Amines to Alkoxyl Radicals
    Sisti, Sergio
    Ioele, Fabio
    Scarchilli, Filippo
    Galeotti, Marco
    Dilabio, Gino A.
    Salamone, Michela
    Bietti, Massimo
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 26 (37)
  • [44] Transition Metal-Doped C20 Fullerene-Based Single-Atom Catalysts with High Catalytic Activity for Hydrogen Dissociation Reaction
    Sarfaraz, Sehrish
    Yar, Muhammad
    Sheikh, Nadeem S.
    Bayach, Imene
    Ayub, Khurshid
    ACS OMEGA, 2023, 8 (15): : 14077 - 14088
  • [45] Syntheses of Trifluoroethylated N-Heterocycles from Vinyl Azides and Togni's Reagent Involving 1,n-Hydrogen-Atom Transfer Reactions
    Terhorst, Steven
    Tiwari, Deo Prakash
    Meister, Daniela
    Petran, Benedict
    Rissanen, Kari
    Bolm, Carsten
    ORGANIC LETTERS, 2020, 22 (12) : 4766 - 4770
  • [46] Direct alkene functionalization via photocatalytic hydrogen atom transfer from C(sp3)-H compounds: a route to pharmaceutically important molecules
    Fan, Hangqian
    Fang, Yuxin
    Yu, Jingbo
    CHEMICAL COMMUNICATIONS, 2024, 60 (94) : 13796 - 13818
  • [47] Electronic control over site-selectivity in hydrogen atom transfer (HAT) based C(sp3)-H functionalization promoted by electrophilic reagents
    Galeotti, Marco
    Salamone, Michela
    Bietti, Massimo
    CHEMICAL SOCIETY REVIEWS, 2022, 51 (06) : 2171 - 2223
  • [48] Asymmetric Michael reaction of arylacetyl phosphonates to nitroalkenes with bifunctional amine-thiourea catalyst bearing multiple-hydrogen-bond donor: efficient construction of chiral α-substituted carboxylic ester compounds
    Zhang, Ming-Liang
    Chen, Lin
    You, Yong
    Wang, Zhen-Hua
    Yue, Deng-Feng
    Zhang, Xiao-Mei
    Xu, Xiao-Ying
    Yuan, Wei-Cheng
    TETRAHEDRON, 2016, 72 (21) : 2677 - 2682
  • [49] Factors Governing Reactivity and Selectivity in Hydrogen Atom Transfer from C(sp3)-H Bonds of Nitrogen-Containing Heterocycles to the Cumyloxyl Radical
    Galeotti, Marco
    Trasatti, Chiara
    Sisti, Sergio
    Salamone, Michela
    Bietti, Massimo
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (11) : 7456 - 7463
  • [50] Visible-Light-Mediated Synthesis of 1,2,4-Dithiazolidines from β-Ketothioamides through a Hydrogen-Atom-Transfer Photocatalytic Approach of Eosin Y
    Ansari, Monish A.
    Yadav, Dhananjay
    Soni, Sonam
    Srivastava, Abhijeet
    Singh, Maya Shankar
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (09) : 5404 - 5412
12345