Synthesis of β-Keto Sulfones by Oxy-Sulfonylation of Alkynes in HFIP

被引：11
作者：
Chen, Xingyu [1 ,2 ,5 ]
Lu, Sixian [1 ,2 ]
Zheng, Yuyan [3 ,4 ]
Wang, Jigang [1 ,2 ]
Yang, Lan [1 ,2 ]
Sun, Peng [1 ,2 ]
机构：
[1] Chinese Acad Med Sci, Inst Chinese Mat Med, Beijing 100700, Peoples R China
[2] Chinese Acad Med Sci, Artemisinin Res Ctr, Beijing 100700, Peoples R China
[3] Jinan Univ, Sch Clin Med 2, Shenzhen Peoples Hosp, Dept Stomatol, Guangzhou, Peoples R China
[4] Southern Univ Sci & Technol, Affiliated Hosp 1, Shenzhen 518020, Peoples R China
[5] Chengdu Univ, Sch Pharm, Chengdu 610106, Peoples R China
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2022年 / 364卷 / 07期
基金：
中国国家自然科学基金;
关键词：
Aerobic oxidation; Sulfonylation; HFIP; beta-Keto sulfones; TERMINAL ALKYNES; AEROBIC DIFUNCTIONALIZATION; RADICAL REACTION; GREEN CHEMISTRY; SULFINIC ACIDS; HYDROARYLATION; INHIBITORS; OXIDATION; ALKENES; OLEFINS;
D O I：
10.1002/adsc.202101444
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
Herein, we have established a method for the construction of beta-keto sulfones through aerobic oxy-sulfonylation of alkynes with sulfinates. The reaction performed employing air as the oxidant and oxygen source. Moreover, this protocol exhibits low consume of sulfinates, short reaction period, and minimal waste. Mechanism study and density functional theory (DFT) calculation showed that the solvent played a significant role in the transformation.
引用
收藏
页码：1305 / 1312
页数：8
相关论文
共 66 条
[1]   Synthesis of N-benzenesulfonamide-1H-pyrazoles bearing arylsulfonyl moiety: Novel celecoxib analogs as potent anti-inflammatory agents [J].
Abdel-Aziz, Hatem A. ;
Al-Rashood, Khalid A. ;
ElTahir, Kamal Eldin H. ;
Suddek, Ghada M. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2014, 80 :416-422
[2]   Green Chemistry: Principles, Applications, and Disadvantages [J].
Abdussalam-Mohammed, Wanisa ;
Ali, Amna Qasem ;
Errayes, Asma O. .
CHEMICAL METHODOLOGIES, 2020, 4 (04) :408-423
[3]  
[Anonymous], 2014, ANGEW CHE, DOI DOI 10.1039/C4GC00542B
[4]   Synthesis of Quinolines: A Green Perspective [J].
Batista, Vasco F. ;
Pinto, Diana C. G. A. ;
Silva, Artur M. S. .
ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2016, 4 (08) :4064-4078
[5]   Predicting the stability of aprotic solvents in Li-air batteries: pKa calculations of aliphatic C-H acids in dimethyl sulfoxide [J].
Bryantsev, Vyacheslav S. .
CHEMICAL PHYSICS LETTERS, 2013, 558 :42-47
[6]   Temperature-Controlled Desulfonylative Condensation of α-Sulfonyl o-Hydroxyacetophenones and 2-Formyl Azaarenes: Synthesis of Azaaryl Aurones and Flavones [J].
Chang, Meng-Yang ;
Chen, Han-Yu ;
Tsai, Yu-Lin .
JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (01) :326-337
[7]   TBHP-Mediated Oxidative Decarboxylative Cyclization in Water: Direct and Sustainable Access to Anti-malarial Polycyclic Fused Quinazolinones and Rutaecarpine [J].
Chen, Xingyu ;
Xia, Fei ;
Zhao, Yifan ;
Ma, Ji ;
Ma, Yue ;
Zhang, Dong ;
Yang, Lan ;
Sun, Peng .
CHINESE JOURNAL OF CHEMISTRY, 2020, 38 (11) :1239-1244
[8]   Hydroarylation of Alkenes Using Anilines in Hexafluoroisopropanol [J].
Colomer, Ignacio .
ACS CATALYSIS, 2020, 10 (11) :6023-6029
[9]   Hydrogen Bonding to Hexafluoroisopropanol Controls the Oxidative Strength of Hypervalent Iodine Reagents [J].
Colomer, Ignacio ;
Batchelor-McAuley, Christopher ;
Odell, Barbara ;
Donohoe, Timothy J. ;
Compton, Richard G. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (28) :8855-8861
[10]   Metrics to 'green' chemistry - which are the best? [J].
Constable, DJC ;
Curzons, AD ;
Cunningham, VL .
GREEN CHEMISTRY, 2002, 4 (06) :521-527
1234567