DMSO as a Switchable Alkylating Agent in Heteroarene C-H Functionalization

被引:55
作者
Garza-Sanchez, R. Aleyda [1 ]
Patra, Tuhin [1 ]
Tlahuext-Aca, Adrian [1 ]
Strieth-Kalthoff, Felix [1 ]
Glorius, Frank [1 ]
机构
[1] Westfalische Wilhelms Univ Munster, Organ Chem Inst, Corrensstr 40, D-48149 Munster, Germany
关键词
C-H functionalization; heteroarenes; methylation; methylthiomethylation; photoredox catalysis; NUCLEOPHILIC CHARACTER; COMBINING PHOTOREDOX; DIMETHYL-SULFOXIDE; METHYLATION; OXIDATION; RADICALS; ALCOHOLS; ACIDS; GENERATION; CATALYSIS;
D O I
10.1002/chem.201802352
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Herein, we report a novel strategy for the activation of DMSO to act as a versatile alkylating agent in heteroarene C-H functionalization. This direct, simple, and mild switch between methylation/trideuteromethylation and methylthiomethylation of heteroarenes was achieved under reagent-controlled photoredox catalysis conditions. The proposed mechanism is supported by both experimental and computational studies.
引用
收藏
页码:10064 / 10068
页数:5
相关论文
共 61 条
[1]  
[Anonymous], 2017, ANGEW CHEM
[2]  
[Anonymous], 2014, ANGEW CHEM, V126, P7272, DOI DOI 10.1002/ange.201403590
[3]   Alkene synthesis: elimination of arenesulfinic acid from alkyl aryl sulfones using potassium trimethylsilanolate as base [J].
Baker-Glenn, CAG ;
Barrett, AGM ;
Gray, AA ;
Procopiou, PA ;
Ruston, M .
TETRAHEDRON LETTERS, 2005, 46 (43) :7427-7430
[4]   GENERATION OF RADICALS FROM SULPHOXIDES WITH FENTONS REAGENT - NEW RADICAL ALKYLATION METHOD [J].
BERTILSS.BM ;
GUSTAFSS.B ;
KUHN, I ;
TORSSELL, K .
ACTA CHEMICA SCANDINAVICA, 1970, 24 (10) :3590-&
[5]   Radical trideuteromethylation with deuterated dimethyl sulfoxide in the synthesis of heterocycles and labelled building blocks [J].
Caporaso, Roberta ;
Manna, Srimanta ;
Zinken, Sarah ;
Kochnev, Alexander R. ;
Lukyanenko, Evgeny R. ;
Kurkin, Alexander V. ;
Antonchick, Andrey P. .
CHEMICAL COMMUNICATIONS, 2016, 52 (84) :12486-12489
[6]   Photoredox/Bronsted Acid Co-Catalysis Enabling Decarboxylative Coupling of Amino Acid and Peptide Redox-Active Esters with N-Heteroarenes [J].
Cheng, Wan-Min ;
Shang, Rui ;
Fu, Yao .
ACS CATALYSIS, 2017, 7 (01) :907-911
[7]   Methylation of 2′-Deoxyguanosine by a Free Radical Mechanism [J].
Crean, Conor ;
Geacintov, Nicholas E. ;
Shafirovich, Vladimir .
JOURNAL OF PHYSICAL CHEMISTRY B, 2009, 113 (38) :12773-12781
[8]   Regioselective Ene-Type Allylic Chlorination of Electron-Rich Alkenes by Activated DMSO [J].
Demertzidou, Vera P. ;
Pappa, Stavroula ;
Sarli, Vasiliki ;
Zografos, Alexandros L. .
JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (16) :8710-8715
[9]  
DiRocco D.A., 2014, ANGEW CHEM INT EDIT, V126, P4902, DOI [DOI 10.1002/ANGE.201402023, 10.1002/ange.201402023]
[10]   Late-Stage Functionalization of Biologically Active Heterocycles Through Photoredox Catalysis [J].
DiRocco, Daniel A. ;
Dykstra, Kevin ;
Krska, Shane ;
Vachal, Petr ;
Conway, Donald V. ;
Tudge, Matthew .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (19) :4802-4806