Metal-Free Oxidative Radical Addition of Carbonyl Compounds to α,α-Diaryl Allylic Alcohols: Synthesis of Highly Functionalized Ketones

被引:71
|
作者
Chu, Xue-Qiang [1 ,2 ]
Meng, Hua [1 ,2 ]
Zi, You [1 ,2 ]
Xu, Xiao-Ping [1 ,2 ]
Ji, Shun-Jun [1 ,2 ]
机构
[1] Soochow Univ, Key Lab Organ Synth Jiangsu Prov, Coll Chem Chem Engn & Mat Sci, Suzhou 215123, Peoples R China
[2] Soochow Univ, Collaborat Innovat Ctr Suzhou Nano Sci & Technol, Suzhou 215123, Peoples R China
关键词
allylic compounds; 1,2-aryl migration; dicarbonyl compounds; domino reactions; radical reactions; EFFICIENT SYNTHESIS; CATALYZED TRIFLUOROMETHYLATION; BOND FUNCTIONALIZATION; SIMPLE ALKANES; CYCLIC ETHERS; C(SP(3))-H; INSERTION; ALKENES; REARRANGEMENT; ALKENYLATION;
D O I
10.1002/chem.201404463
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A metal-free direct alkylation of simple carbonyl compounds (ketones, esters, and amides) with alpha,alpha-diaryl allylic alcohols is described. The protocol provides facile access to highly functionalized dicarbonyl ketones by a radical addition/1,2-aryl migration cascade. The regioselectivity of the reaction was precisely controlled by the nature of the carbonyl compound.
引用
收藏
页码:17198 / 17206
页数:9
相关论文
共 50 条
  • [1] Metal-free oxidative direct C(sp3)-H bond functionalization of ethers with α,α-diaryl allylic alcohols
    Chu, Xue-Qiang
    Meng, Hua
    Zi, You
    Xu, Xiao-Ping
    Ji, Shun-Jun
    [J]. CHEMICAL COMMUNICATIONS, 2014, 50 (68) : 9718 - 9721
  • [2] Metal-free oxidative synthesis of benzimidazole compounds by dehydrogenative coupling of diamines and alcohols
    Hu, Jiaming
    Li, Mengjia
    Wan, Jing
    Sun, Jinnan
    Gao, Hu
    Zhang, Feng
    Zhang, Zhibing
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (14) : 2852 - 2856
  • [3] Metal-free synthesis of ketones by visible-light induced aerobic oxidative radical addition of aryl hydrazines to alkenes
    Ding, Ya
    Zhang, Wenkai
    Li, Hao
    Meng, Yunge
    Zhang, Te
    Chen, Qiu-Yun
    Zhu, Chunyin
    [J]. GREEN CHEMISTRY, 2017, 19 (13) : 2941 - 2944
  • [4] Metal-free oxidative functionalization of C(sp3)-H of ketones and alcohols for the synthesis of isoquinolinonediones
    Zhu, Su-Li
    Zhou, Ping-Xin
    Xia, Xiao-Feng
    [J]. RSC ADVANCES, 2016, 6 (68): : 63325 - 63330
  • [5] Synthesis of α-sulfenylated carbonyl compounds under metal-free conditions
    Mou, Dan
    Wu, Yuanyuan
    Wang, Linda
    Fu, Ying
    Du, Zhengyin
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (02) : 274 - 278
  • [6] Synthesis of Highly Functionalized Pyridines: A Metal-Free Cascade Process
    Wei, Kai
    Sun, Yu-Cui
    Li, Rui
    Zhao, Jing-Feng
    Chen, Wen
    Zhang, Hongbin
    [J]. ORGANIC LETTERS, 2021, 23 (17) : 6669 - 6673
  • [7] Synthesis of highly functionalized propargylic alcohols:: Direct addition of epoxy acetylides to aldehydes and ketones
    Hoffmann-Röder, A
    Krause, N
    [J]. HELVETICA CHIMICA ACTA, 2002, 85 (10) : 3176 - 3184
  • [8] Halide-free and metal-free allylic thiolation/selenation of P(O)H compounds with sulfur/selenium and allylic alcohols
    Zhu, Longzhi
    Luo, Weiwei
    Guo, Furong
    Chen, Lin
    Tang, Ying
    Xiong, Biquan
    Liu, Yu
    Tang, Ke-Wen
    Qiu, Renhua
    [J]. GREEN CHEMISTRY, 2024, : 10886 - 10892
  • [9] Metal-free oxidative C(sp3)-H bond functionalization of alkanes and alkylation-initiated radical 1,2-aryl migration in α,α-diaryl allylic alcohols
    Zhao, Jincan
    Fang, Hong
    Song, Ruichun
    Zhou, Jie
    Han, Jianlin
    Pan, Yi
    [J]. CHEMICAL COMMUNICATIONS, 2015, 51 (03) : 599 - 602
  • [10] Metal-free [3+2+1] annulation of allylic alcohols, ketones, and ammonium acetate: radical-involving synthesis of 2,3-diarylpyridine derivatives
    Ge, Danhua
    Luo, Xin-Long
    Tang, Xi
    Pang, Chao-Bin
    Wang, Xin
    Chu, Xue-Qiang
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (10) : 2277 - 2283