Use of Hypervalent Iodine Reagents in Visible Light-Promoted α-Ketoacylations of Sulfoximines with Aryl Alkynes

被引:27
作者
Wang, Chenyang [1 ]
Ma, Ding [1 ]
Tu, Yongliang [1 ]
Bolm, Carsten [1 ]
机构
[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
关键词
D O I
10.1021/acs.orglett.0c03338
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In visible light, sulfoximidoyl-containing hypervalent iodine reagents react with aryl alkynes to give N-alpha-ketoacylated sulfoximines in good to high yields. The process is metal- and base-free, providing the diketonic products without the use of highly oxygenated reagents such as peroxides. Results from mechanistic investigations suggest the intermediacy of radicals and reveal the importance of molecular oxygen.
引用
收藏
页码:8937 / 8940
页数:4
相关论文
共 52 条
[1]   Synthesis of α-Keto-Imides via Oxidation of Ynamides [J].
Al-Rashid, Ziyad F. ;
Johnson, Whitney L. ;
Hsung, Richard P. ;
Wei, Yonggang ;
Yao, Pei-Yuan ;
Liu, Renhei ;
Zhao, Kang .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (22) :8780-8784
[2]  
[Anonymous], 2013, HYPERVALENT IODINE C, DOI DOI 10.1002/9781118341155
[3]  
Bacci L., 2018, Journal of Entomological and Acarological Research, V50, P51, DOI 10.4081/jear.2018.7836
[4]  
BOLM C, 1992, SYNLETT, P439
[5]   Electrochemical Synthesis of α-Ketoamides under Catalyst-, Oxidant-, and Electrolyte-Free Conditions [J].
Chen, Jin-Yang ;
Wu, Hong-Yu ;
Gui, Qing-Wen ;
Han, Xiao-Ran ;
Wu, Yan ;
Du, Kui ;
Cao, Zhong ;
Lin, Ying-Wu ;
He, Wei-Min .
ORGANIC LETTERS, 2020, 22 (06) :2206-2209
[6]   Copper-Catalyzed N-Alkynylations of Sulfoximines with Bromoacetylenes [J].
Chen, Xiao Yun ;
Wang, Long ;
Frings, Marcus ;
Bolm, Carsten .
ORGANIC LETTERS, 2014, 16 (14) :3796-3799
[7]   Copper-Catalyzed Oxidative -Ketoacylations of Sulfoximines with Aryl Methyl Ketones and Dioxygen as Terminal Oxidant [J].
Cheng, Hanchao ;
Bolm, Carsten .
SYNLETT, 2016, 27 (05) :769-772
[8]   Recent Developments in General Methodologies for the Synthesis of α-Ketoamides [J].
De Risi, Carmela ;
Pollini, Gian Piero ;
Zanirato, Vinicio .
CHEMICAL REVIEWS, 2016, 116 (05) :3241-3305
[9]   A general metal free approach to α-ketoamides via oxidative amidation-diketonization of terminal alkynes [J].
Deshidi, Ramesh ;
Kumar, Manjeet ;
Devari, Shekaraiah ;
Shah, Bhahwal Ali .
CHEMICAL COMMUNICATIONS, 2014, 50 (67) :9533-9535
[10]   Enantioselective Iodine(I/III) Catalysis in Organic Synthesis [J].
Flores, Andrea ;
Cots, Eric ;
Berges, Julien ;
Muniz, Kilian .
ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (01) :2-25