Aerobic Benzylic C(sp3)-H Bond Oxygenations Catalyzed by NBS under Visible Light Irradiation

被引:8
作者
Ye, Taiqiang [1 ]
Li, Yuzheng [1 ]
Ma, Yanni [2 ]
Tan, Shenpeng [1 ]
Li, Feng [1 ]
机构
[1] Yantai Univ, Sch Pharm, Collaborat Innovat Ctr Adv Drug Delivery Syst & Bi, Key Lab Mol Pharmacol & Drug Evaluat,Minist Educ, Yantai 264005, Peoples R China
[2] Henan Acad Sci, Henan Nat Prod Biotechnol Co LTD, Zhengzhou 450002, Peoples R China
关键词
SP(3) C-H; ALPHA-OXYGENATION; MOLECULAR-OXYGEN; OXIDATION; BENZYLPYRIDINES; ISOFLAVONOIDS; C-SP(3)-H;
D O I
10.1021/acs.joc.3c02284
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient photocatalytic oxidation of benzylic C(sp(3))-H bonds to ketones, esters, and amides has been developed using NBS as a metal-free photocatalyst and O-2 as an oxidant. A variety of synthetically and biologically valuable compounds are assembled in moderate to excellent yields. The synthetic utility of this approach has been demonstrated by gram-scale experiments. A possible free radical mechanism was proposed to rationalize the reaction procedure.
引用
收藏
页码:534 / 540
页数:7
相关论文
共 37 条
[1]   Aerobic α-Oxidation of N-Substituted Tetrahydroisoquinolines to Dihydroisoquinolones via Organo-photocatalysis [J].
Aganda, Kim Christopher C. ;
Hong, Boseok ;
Lee, Anna .
ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (05) :1124-1129
[2]   Total Synthesis of a Noricumazole A Library and Evaluation of HCV Inhibition [J].
Barbier, Jenny ;
Wegner, Jens ;
Benson, Stefan ;
Gentzsch, Juliane ;
Pietschmann, Thomas ;
Kirschning, Andreas .
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (29) :9083-9090
[3]   Dioxygen: What Makes This Triplet Diradical Kinetically Persistent? [J].
Borden, Weston Thatcher ;
Hoffmann, Roald ;
Stuyver, Thijs ;
Chen, Bo .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (26) :9010-9018
[4]  
Buss A. D., 2010, Natural ProductChemistry for Drug Discovery
[5]   Metal-free allylic/benzylic oxidation strategies with molecular oxygen: recent advances and future prospects [J].
Chen, Kexian ;
Zhang, Pengfei ;
Wang, Yong ;
Li, Haoran .
GREEN CHEMISTRY, 2014, 16 (05) :2344-2374
[6]   A g-C3N4-based heterogeneous photocatalyst for visible light mediated aerobic benzylic C-H oxygenations [J].
Geng, Pengxin ;
Tang, Yurong ;
Pan, Guangtong ;
Wang, Wentao ;
Hu, Jinchuan ;
Cai, Yunfei .
GREEN CHEMISTRY, 2019, 21 (22) :6116-6122
[7]   Dehydrogenative α-Oxygenation of Ethers with an Iron Catalyst [J].
Gonzalez-de-Castro, Angela ;
Robertson, Craig M. ;
Xiao, Jianliang .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (23) :8350-8360
[8]   Metal-Free Halogen(I) Catalysts for the Oxidation of Aryl(heteroaryl)methanes to Ketones or Esters: Selectivity Control by Halogen Bonding [J].
Guha, Somraj ;
Sekar, Govindasamy .
CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (53) :14171-14182
[9]   Synthesis of structurally diverse diarylketones through the diarylmethyl sp3 C-H oxidation [J].
He, Chao ;
Zhang, Xiaohui ;
Huang, Ruofeng ;
Pan, Jing ;
Li, Jiaqiang ;
Ling, Xuege ;
Xiong, Yan ;
Zhu, Xiangming .
TETRAHEDRON LETTERS, 2014, 55 (32) :4458-4462
[10]   Co/NHPI-mediated aerobic oxygenation of benzylic C-H bonds in pharmaceutically relevant molecules [J].
Hruszkewycz, Damian P. ;
Miles, Kelsey C. ;
Thiel, Oliver R. ;
Stahl, Shannon S. .
CHEMICAL SCIENCE, 2017, 8 (02) :1282-1287