Radical Cross-Coupling Reaction of NPIB Ester with Sodium Sulfinate Salts for the Synthesis of Sulfones

被引:0
作者
Shah, Syed Anis Ali [1 ,2 ]
Liu, Bo-Xi [1 ,2 ]
Hasan, Muhammad [1 ,2 ]
Peng, Jing-Han [1 ,2 ]
Rao, WeiDong [3 ]
Shen, Shu-Su [4 ]
Sheng, DaoPeng [5 ,6 ]
Wang, Shun-Yi [1 ,2 ]
机构
[1] Soochow Univ, Coll Chem Chem Engn & Mat Sci, Key Lab Organ Synth Jiangsu Prov, Suzhou 215123, Peoples R China
[2] Soochow Univ, Collaborat Innovat Ctr Suzhou Nano Sci & Technol, Suzhou 215123, Peoples R China
[3] Nanjing Forestry Univ, Coll Chem Engn, Key Lab Biomass Based Green Fuels & Chem, Nanjing 210037, Peoples R China
[4] Suzhou Univ Sci & Technol, Sch Environm Sci & Engn, Suzhou 215009, Peoples R China
[5] Soochow Univ, Sch Radiol & Interdisciplinary Sci RAD X, Suzhou 215123, Jiangsu, Peoples R China
[6] Soochow Univ, Collaborat Innovat Ctr Radiat Med Jiangsu Higher E, Suzhou 215123, Jiangsu, Peoples R China
基金
中国国家自然科学基金;
关键词
REDOX-ACTIVE ESTERS; TERTIARY ALCOHOLS; SULFUR-DIOXIDE; QUATERNARY; CONSTRUCTION; N-(ACYLOXY)PHTHALIMIDES; SULFONYLATION; CENTERS;
D O I
10.1021/acs.joc.5c01135
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Herein, we report decarboxylative sulfonylation involving alpha-N-phthalimido-oxy isobutyrate (NPIB) as a radical precursor. We successfully developed different NPIBs from N-hydroxyphthalimide and alkyl butyl isobutyrate and subjected them to reactions with easily available sodium sulfinate salts as the sulfonylating source. A successful reaction was executed using Cu/4-CzIPN as dual catalysts under blue LED irradiation. The reaction featured functional group tolerance, compatibility with a wide range of sodium sulfinate salts, easily accessible starting materials, and moderate reaction conditions.
引用
收藏
页码:9200 / 9209
页数:10
相关论文
共 37 条
[1]   Radical Deoxyfunctionalisation Strategies [J].
Anwar, Khadijah ;
Merkens, Kay ;
Aguilar Troyano, Francisco Jose ;
Gomez-Suarez, Adrian .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (26)
[2]   THE INVENTION OF RADICAL REACTIONS .17. A DECARBOXYLATIVE SULFONYLATION OF CARBOXYLIC-ACIDS [J].
BARTON, DHR ;
LACHER, B ;
MISTERKIEWICZ, B ;
ZARD, SZ .
TETRAHEDRON, 1988, 44 (04) :1153-1158
[3]   FORMATION OF QUATERNARY CARBON CENTERS FROM TERTIARY ALCOHOLS BY FREE-RADICAL METHODS [J].
BARTON, DHR ;
CRICH, D .
TETRAHEDRON LETTERS, 1985, 26 (06) :757-760
[4]   NEW METHOD FOR DEOXYGENATION OF SECONDARY ALCOHOLS [J].
BARTON, DHR ;
MCCOMBIE, SW .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (16) :1574-1585
[5]   Synthetic Strategies toward Natural Products Containing Contiguous Stereogenic Quaternary Carbon Atoms [J].
Bueschleb, Martin ;
Dorich, Stephane ;
Hanessian, Stephen ;
Tao, Daniel ;
Schenthal, Kyle B. ;
Overman, Larry E. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (13) :4156-4186
[6]   Alcohol-alcohol cross-coupling enabled by SH2 radical sorting [J].
Chen, Ruizhe ;
Intermaggio, Nicholas E. ;
Xie, Jiaxin ;
Rossi-Ashton, James A. ;
Gould, Colin A. ;
Martin, Robert T. ;
Alcazar, Jesus ;
MacMillan, David W. C. .
SCIENCE, 2024, 383 (6689) :1350-1357
[7]   Metallaphotoredox-enabled deoxygenative arylation of alcohols [J].
Dong, Zhe ;
MacMillan, David W. C. .
NATURE, 2021, 598 (7881) :451-+
[8]   Recent advances in the synthesis of vinyl sulfones [J].
Fang, Yuyu ;
Luo, Zaigang ;
Xu, Xuemei .
RSC ADVANCES, 2016, 6 (64) :59661-59676
[9]   Carbon quaternization of redox active esters and olefins by decarboxylative coupling [J].
Gan, Xu-cheng ;
Zhang, Benxiang ;
Dao, Nathan ;
Bi, Cheng ;
Pokle, Maithili ;
Kan, Liyan ;
Collins, Michael R. ;
Tyrol, Chet C. ;
Bolduc, Philippe N. ;
Nicastri, Michael ;
Kawamata, Yu ;
Baran, Phil S. ;
Shenvi, Ryan .
SCIENCE, 2024, 384 (6691) :113-118
[10]   A New Avenue toward Androgen Receptor Pan-antagonists: C2 Sterically Hindered Substitution of Hydroxy-propanamides [J].
Guerrini, Andrea ;
Tesei, Anna ;
Ferroni, Claudia ;
Paganelli, Giulia ;
Zamagni, Alice ;
Carloni, Silvia ;
Di Donato, Marzia ;
Castoria, Gabriella ;
Leonetti, Carlo ;
Porru, Manuela ;
De Cesare, Michelandrea ;
Zaffaroni, Nadia ;
Beretta, Giovanni Luca ;
Del Rio, Alberto ;
Varchi, Greta .
JOURNAL OF MEDICINAL CHEMISTRY, 2014, 57 (17) :7263-7279