Site-selective amination and/or nitrilation via metal-free C(sp2)-C(sp3) cleavage of benzylic and allylic alcohols

被引：10
|
作者：
Anugu, Raghunath Reddy [1 ]
Falck, John R. [1 ]
机构：
[1] Univ Texas Southwestern Med Ctr Dallas, Dept Biochem, Dept Pharmacol, Div Chem, Dallas, TX 75390 USA
来源：
CHEMICAL SCIENCE | 2022年 / 13卷 / 17期
关键词：
C BOND-CLEAVAGE; CARBOXYLIC-ACIDS; H AMINATION; N-H; KETONES; OXYGENATION; MECHANISM; OXIDATION; ANILINES; NITROGEN;
D O I：
10.1039/d2sc00758d
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Benzylic/allylic alcohols are converted via site-selective C(sp(2))-C(sp(3)) cleavage to value-added nitrogenous motifs, viz., anilines and/or nitriles as well as N-heterocycles, utilizing commercial hydroxylamine-O-sulfonic acid (HOSA) and Et3N in an operationally simple, one-pot process. Notably, cyclic benzylic/allylic alcohols undergo bis-functionalization with attendant increases in architectural complexity and step-economy.
引用
收藏
页码：4821 / 4827
页数：7
相关论文
共 50 条
  • [31] Site-Selective C(sp3)-H and C(sp2)-H Functionalization of Amines Using a Directing-Group-Guided Strategy
    Kapoor, Mohit
    Singh, Adhish
    Sharma, Kirti
    Hua Hsu, Ming
    ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (21) : 4513 - 4542
  • [32] Metal-free C-3 selective C(sp2)-C(sp3) heteroarylation of anilines with imidazo[1,2-a]pyridine derivatives via cross-dehydrogenative coupling
    Wang, Kai
    Du, Xiaoxue
    Zhang, Pengfei
    Wei, Zhenjiang
    Cao, Xian-Ting
    RSC ADVANCES, 2023, 13 (31) : 21685 - 21689
  • [33] Metal-Free Cyclopropanol Ring-Opening C(sp3)-C(sp2) Cross-Couplings with Aryl Sulfoxides
    Chen, Dengfeng
    Fu, Yuanyuan
    Cao, Xiaoji
    Luo, Jinyue
    Wang, Fei
    Huang, Shenlin
    ORGANIC LETTERS, 2019, 21 (14) : 5600 - 5605
  • [34] Selective Oxidative Decarbonylative Cleavage of Unstrained C(sp3)-C(sp2) Bond: Synthesis of Substituted Benzoxazinones
    Verma, Ajay
    Kumar, Sangit
    ORGANIC LETTERS, 2016, 18 (17) : 4388 - 4391
  • [35] A General Catalyst for Site-Selective C(sp3)-H Bond Amination of Activated Secondary over Tertiary Alkyl C(sp3)-H Bonds
    Scamp, Ryan J.
    Jirak, James G.
    Dolan, Nicholas S.
    Guzei, Ilia A.
    Schomaker, Jennifer M.
    ORGANIC LETTERS, 2016, 18 (12) : 3014 - 3017
  • [36] Direct Benzylic C(sp3)-O Coupling with Alcohol via Site-Selective C(sp3)-H Cleavage at Room Temperature through a Remote Directing Group-Enabled Radical Relay Strategy
    Wang, Fang
    Chen, Jiaming
    Jia, Xiaoqi
    Zhuang, Dailin
    Wan, Zhenyang
    Ma, Lifang
    Li, Ziyuan
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (16): : 10698 - 10709
  • [37] Photocatalyzed Site-Selective C(sp3)-H Functionalization of Alkylpyridines at Non-Benzylic Positions
    Fukuyama, Takahide
    Nishikawa, Tomohiro
    Yamada, Keiichi
    Ravelli, Davide
    Fagnoni, Maurizio
    Ryu, Ilhyong
    ORGANIC LETTERS, 2017, 19 (23) : 6436 - 6439
  • [38] Recent Progress in Amination Enabled by Transition-Metal-Free C(sp2)-O/C(sp2)-S Bond Cleavage Strategy
    Lia, Shen-Huan
    Longa, Cheng-Yu
    Yang, Xin-Ge
    Wang, Xue-Qiang
    SYNTHESIS-STUTTGART, 2021, 53 (20): : 3716 - 3724
  • [39] Stereospecific Synthesis of (Z,Z)-Isobenzofurans via Radical-Enabled Cleavage of C(sp3)-C(sp3) and C(sp2)-Halogen Bonds
    Huang, Min-Hua
    Shi, Hao-Nan
    Zhu, Chi-Fan
    He, Chun-Lan
    Hao, Wen-Juan
    Tu, Shu-Jiang
    Jiang, Bo
    ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (23) : 5340 - 5345
  • [40] Copper-catalyzed transfer methylenation via C(sp3)-C(sp3) bond cleavage of alcohols
    Hong, Chuan-Ming
    Zhuang, Xin
    Luo, Zhen
    Xiong, Si-Qi
    Liu, Zheng-Qiang
    Li, Qing-Lin
    Zou, Fei-Fei
    Li, Qing-Hua
    Liu, Tang-Lin
    ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (23) : 6547 - 6555
12345