Photochemical Synthesis of S,N,O-Containing Polyheterocycles via an a-C(sp3)-H Functionalization/Radical Cyclization Cascade

被引:9
作者
Cheng, Shi-Yan [1 ]
Liao, Jia-Bin [1 ]
Lin, Yu-Mei [1 ]
Gong, Lei [1 ,2 ]
机构
[1] Xiamen Univ, Coll Chem & Chem Engn, Key Lab Chem Biol Fujian Prov, Xiamen 361005, Peoples R China
[2] Innovat Lab Sci & Technol Energy Mat Fujian Prov, Xiamen 361005, Peoples R China
基金
中国国家自然科学基金;
关键词
C-H ALKYLATION; PHOTOREDOX CATALYSIS; METHYL SULFIDES; N-ENYNES; ALKENES; BOND;
D O I
10.1021/acs.orglett.3c02423
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A highly effective approach based on an organophotocatalytic a-C(sp(3))-H functionalization/radical cyclization cascade has been developed. This method enables the synthesis of various tricyclic heterocycles containing S, O, and N atoms with excellent site selectivity and diastereoselectivity. Mechanistic investigations have confirmed that the reaction involves photoredox-triggered C(sp(3))-H cleavage followed by a radical cyclization and aromatization process. These findings are expected to pave the way for developing cost-effective tandem radical reactions and synthesizing heterocyclic drugs.
引用
收藏
页码:6566 / 6570
页数:5
相关论文
共 31 条
[1]   α-Heteroarylation of Thioethers via Photoredox and Weak Bronsted Base Catalysis [J].
Alfonzo, Edwin ;
Hande, Sudhir M. .
ORGANIC LETTERS, 2021, 23 (15) :6115-6120
[2]   Photoredox and Weak Bronsted Base Dual Catalysis: Alkylation of α-Thio Alkyl Radicals [J].
Alfonzo, Edwin ;
Hande, Sudhir M. .
ACS CATALYSIS, 2020, 10 (21) :12590-12595
[3]   Electrochemical no-carrier-added radiofluorination of thioethers [J].
Allison, Nathanael ;
Balandeh, Mehrdad ;
Holloway, Travis ;
Gomez, Adrian ;
Rios, Alejandra ;
Waldmann, Christopher M. ;
Lebedev, Artem ;
Sadeghi, Saman .
JOURNAL OF FLUORINE CHEMISTRY, 2022, 257
[4]  
[Anonymous], 2002, Handbook of Bond Dissociation Energies in Organic Compounds
[5]   Photocatalytic three-component asymmetric sulfonylation via direct C(sp3)-H functionalization [J].
Cao, Shi ;
Hong, Wei ;
Ye, Ziqi ;
Gong, Lei .
NATURE COMMUNICATIONS, 2021, 12 (01)
[6]  
Fan XZ, 2018, ANGEW CHEM INT EDIT, V57, P8514, DOI [10.1002/ange.201803220, 10.1002/anie.201803220]
[7]   Sulfur Containing Scaffolds in Drugs: Synthesis and Application in Medicinal Chemistry [J].
Feng, Minghao ;
Tang, Bingqing ;
Liang, Steven H. ;
Jiang, Xuefeng .
CURRENT TOPICS IN MEDICINAL CHEMISTRY, 2016, 16 (11) :1200-1216
[8]   Photocatalytic enantioselective α-aminoalkylation of acyclic imine derivatives by a chiral copper catalyst [J].
Han, Bowen ;
Li, Yanjun ;
Yu, Ying ;
Gong, Lei .
NATURE COMMUNICATIONS, 2019, 10 (1)
[9]   SmI2-catalysed cyclization cascades by radical relay [J].
Huang, Huan-Ming ;
McDouall, Joseph J. W. ;
Procter, David J. .
NATURE CATALYSIS, 2019, 2 (03) :211-218
[10]  
Jiang X., 2018, SULFUR CHEM