Development of a Continuous-Flow Microreactor for Asymmetric Sulfoxidation Using a Biomimetic Manganese Catalyst

被引:19
作者
Dai, Wen [1 ,2 ]
Mi, Yuan [1 ,2 ]
Lv, Ying [1 ,2 ]
Chen, Bo [1 ,2 ]
Li, Guosong [1 ,2 ]
Chen, Guangwen [1 ,2 ]
Gao, Shuang [1 ,2 ]
机构
[1] Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China
[2] Dalian Natl Lab Clean Energy, Dalian 116023, Peoples R China
关键词
asymmetric sulfoxidation; biomimetic process; continuous flow conditions; microreactor; porphyrin-inspired catalyst; HYDROGEN-PEROXIDE; ENANTIOSELECTIVE SYNTHESIS; OXIDATION CATALYSIS; EPOXIDATION; SYSTEM; ORGANOCATALYSIS; SULFIDES; LIGANDS; COMPLEX; ALKENES;
D O I
10.1002/adsc.201501023
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Asymmetric sulfoxidation catalyzed by a biomimetic manganese complex under continuous-flow microreactor is described. The reaction is conducted in microreactor, it can rapidly (<4min) oxidize a wide scope of sulfides with high yield (up to 91%) and excellent enantioselectivity (up to 99% ee), and allows shorter reaction times, easier scale-up and lower catalyst loadings than its batchwise counterpart. Additionally, a convenient numbering-up strategy for the scale-up of asymmetric sulfoxidation has been developed which enables a direct scaling of the reaction to 5g affording the corresponding sulfoxides within 20min.
引用
收藏
页码:667 / 671
页数:5
相关论文
共 59 条
[1]   Role of sulfur chirality in the chemical processes of biology [J].
Bentley, R .
CHEMICAL SOCIETY REVIEWS, 2005, 34 (07) :609-624
[2]  
Bry K. P., 2004, ANGEW CHEM INT EDIT, V43, P5228
[3]  
Bryliakov K. P., 2004, ANGEW CHEM, V116, P5340
[4]  
Cantillo D., 2015, ANGEW CHEM, V127, P6788
[5]   Enantiopure sulfoxides: recent applications in asymmetric synthesis [J].
Carmen Carreno, M. ;
Hernandez-Torres, Gloria ;
Ribagorda, Maria ;
Urbano, Antonio .
CHEMICAL COMMUNICATIONS, 2009, (41) :6129-6144
[6]   Highly efficient oxidation of alcohols catalyzed by a porphyrin-inspired manganese complex [J].
Dai, Wen ;
Lv, Ying ;
Wang, Lianyue ;
Shang, Sensen ;
Chen, Bo ;
Li, Guosong ;
Gao, Shuang .
CHEMICAL COMMUNICATIONS, 2015, 51 (56) :11268-11271
[7]   A Porphyrin-Inspired Iron Catalyst for Asymmetric Epoxidation of Electron-Deficient Olefins [J].
Dai, Wen ;
Li, Guosong ;
Chen, Bo ;
Wang, Lianyue ;
Gao, Shuang .
ORGANIC LETTERS, 2015, 17 (04) :904-907
[8]   Enantioselective oxidation of sulfides with H2O2 catalyzed by a pre-formed manganese complex [J].
Dai, Wen ;
Li, Guosong ;
Wang, Lianyue ;
Chen, Bo ;
Shang, Sensen ;
Lv, Ying ;
Gao, Shuang .
RSC ADVANCES, 2014, 4 (87) :46545-46554
[9]   Asymmetric Epoxidation of Olefins with Hydrogen Peroxide by an in Situ-Formed Manganese Complex [J].
Dai, Wen ;
Shang, Sensen ;
Chen, Bo ;
Li, Guosong ;
Wang, Lianyue ;
Ren, Lanhui ;
Gao, Shuang .
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (14) :6688-6694
[10]   Asymmetric Oxidation Catalysis by a Porphyrin-Inspired Manganese Complex: Highly Enantioselective Sulfoxidation with a Wide Substrate Scope [J].
Dai, Wen ;
Li, Jun ;
Chen, Bo ;
Li, Guosong ;
Lv, Ying ;
Wang, Lianyue ;
Gao, Shuang .
ORGANIC LETTERS, 2013, 15 (22) :5658-5661