Visible-light-driven intramolecular xanthylation of remote unactivated C(sp3)-H bonds

被引：19

作者：

Chen, Hang ^{[2
]}

Zhou, Yang ^{[2
]}

Lei, Panpan ^{[2
]}

Wang, Haifeng ^{[1
]}

Yan, Qiongjiao ^{[1
]}

Properzi, Roberta ^{[5
]}

Wang, Wei ^{[1
]}

Jing, Linhai ^{[1
,2
]}

Chen, Fener ^{[1
,3
,4
]}

机构：

[1] Wuhan Inst Technol, Pharmaceut Res Inst, Wuhan 430205, Peoples R China

[2] China West Normal Univ, Chem Synth & Pollut Control Key Lab Sichuan Prov, Nanchong 637009, Peoples R China

[3] Fudan Univ, Engn Ctr Catalysis & Synth Chiral Mol, Dept Chem, Shanghai 200433, Peoples R China

[4] Shanghai Engn Ctr Ind Catalysis Chiral Drugs, Shanghai 200433, Peoples R China

[5] Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany

来源：

GREEN SYNTHESIS AND CATALYSIS | 2023年 / 4卷 / 04期

基金：

中国国家自然科学基金;

关键词：

C -H functionalization; 5 -Hydrogen atom transfer; Photocatalytic; Site -speci fic; Xanthylation; RADICAL REACTIONS; FUNCTIONALIZATIONS; CHEMISTRY; SKELETON; ROUTE;

D O I：

10.1016/j.gresc.2022.07.003

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Visible light-mediated site-specific C(sp3)-H xanthylation of amides has been accomplished using N-xanthylamides. The N-centered radicals generated by light initiation of N-xanthylamide substrates undergo 1,5-hydrogen atom transfer to form benzylic or alkyl radical intermediates under metal-and catalyst-free conditions. This method exhibits a broad substrate scope, high functional group tolerance, and high regioselectivity. Furthermore, this strategy provides straightforward access to a range of derivatives through the subsequent elaboration of the xanthate group.

引用

页码：350 / 354

页数：5

共 56 条

[1] A NEW RADICAL-BASED SYNTHESIS OF LACTAMS AND INDOLONES FROM DITHIOCARBONATES (XANTHATES)
AXON, J
BOITEAU, L
BOIVIN, J
FORBES, JE
ZARD, SZ
[J]. TETRAHEDRON LETTERS, 1994, 35 (11) : 1719 - 1722
[2] Sulfamate Esters Guide C(3)-Selective Xanthylation of Alkanes
Ayer, Suraj K.
Roizen, J. L.
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (06) : 3508 - 3523
[3] An unusual radical smiles rearrangement
Bacqué, E
El Qacemi, M
Zard, SZ
[J]. ORGANIC LETTERS, 2005, 7 (17) : 3817 - 3820
[4] A concise synthesis of the tricyclic skeleton of pleuromutilin and a new approach to cycloheptenes
Bacqué, E
Pautrat, F
Zard, SZ
[J]. ORGANIC LETTERS, 2003, 5 (03) : 325 - 328
[5] Bergman RG, 2007, NATURE, V446, P391, DOI 10.1038/446391a
[6] A xanthate transfer radical process for the introduction of the trifluoromethyl group
Bertrand, F
Pevere, V
Quiclet-Sire, B
Zard, SZ
[J]. ORGANIC LETTERS, 2001, 3 (07) : 1069 - 1071
[7] Visible-Light-Enabled Decarboxylative Sulfonylation of Cinnamic Acids with Sulfonylhydrazides under Transition-Metal-Free Conditions
Cai, Shunyou
Xu, Yaohui
Chen, Danling
Li, Lihuang
Chen, Qifa
Huang, Mingqiang
Weng, Wen
[J]. ORGANIC LETTERS, 2016, 18 (12) : 2990 - 2993
[8] Radical heteroarylation of unactivated remote C(sp3)-H bonds via intramolecular heteroaryl migration
Cao, Zhu
Zhang, Huihui
Wu, Xinxin
Li, Yahong
Zhu, Chen
[J]. ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (22): : 6395 - 6399
[9] The medicinal chemist's toolbox for late stage functionalization of drug-like molecules
Cernak, Tim
Dykstra, Kevin D.
Tyagarajan, Sriram
Vachal, Petr
Krska, Shane W.
[J]. CHEMICAL SOCIETY REVIEWS, 2016, 45 (03) : 546 - 576
[10] A predictably selective aliphatic C-H oxidation reaction for complex molecule synthesis
Chen, Mark S.
White, M. Christina
[J]. SCIENCE, 2007, 318 (5851) : 783 - 787

← 1 2 3 4 5 6 →