The Preparation of Diaryl Sulfoxinium Triflates and Their Application in Palladium-Catalyzed Cross-Coupling Reactions

被引:3
作者
Wang, Chenyang [1 ]
Wang, Xianliang [1 ]
Kong, Deshen [1 ]
Truong, Khai-Nghi [2 ]
Rissanen, Kari [2 ]
Bolm, Carsten [1 ]
机构
[1] Rhein Westfal TH Aachen, Inst Organ Chem, Landoltweg 1, D-52074 Aachen, Germany
[2] Univ Jyvaskyla, Dept Chem, FI-40014 Jyvaskyla, Finland
关键词
Coupling reaction; Onium salt; Sulfoximine; Sulfoxinium; Triflate; SULFOXIMINES; SALTS; REAGENTS; ARYL; CONVERSION; NITROGEN;
D O I
10.1002/asia.202200828
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Treatment of N-methyl-S,S-diaryl sulfoximines with methyl trifluoromethanesulfonate provides bench-stable sulfoxinium salts in excellent yields. Applying them in Sonogashira-, Heck- and Suzuki-type cross-coupling reactions leads to the corresponding products by sequential C-S bond cleavage and C-C bond formation. Electronic factors induced by substituents on the S-aryl groups govern the coupling efficiency.
引用
收藏
页数:4
相关论文
共 66 条
[1]   Chiral Analogues of PFI-1 as BET Inhibitors and Their Functional Role in Myeloid Malignancies [J].
Altenburg, Bianca ;
Frings, Marcus ;
Schoebel, Jan-Hendrik ;
Gossen, Jonas ;
Pannen, Kristina ;
Vanderliek, Kim ;
Rossetti, Giulia ;
Koschmieder, Steffen ;
Chatain, Nicolas ;
Bolm, Carsten .
ACS MEDICINAL CHEMISTRY LETTERS, 2020, 11 (10) :1928-1934
[2]   Synthesis and Transformations of NH-Sulfoximines [J].
Andresini, Michael ;
Tota, Arianna ;
Degennaro, Leonardo ;
Bull, James A. ;
Luisi, Renzo .
CHEMISTRY-A EUROPEAN JOURNAL, 2021, 27 (69) :17293-17321
[3]  
[Anonymous], 2014, ANGEW CHEM, V126, P794, DOI DOI 10.1002/ANIE.201308484
[4]  
[Anonymous], 2011, ANGEW CHEM, V123, P1925
[5]  
[Anonymous], 1999, ANGEW CHEM, V111, P2577
[6]  
[Anonymous], 2009, Angew. Chem
[7]  
Bacci L., 2018, Journal of Entomological and Acarological Research, V50, P51, DOI [10.4081/jear.2018.7836, 10.4081/jear.2018.7836]
[8]   Recent trends in perfluorinated sulfoximines [J].
Barthelemy, Anne-Laure ;
Magnier, Emmanuel .
COMPTES RENDUS CHIMIE, 2018, 21 (08) :711-722
[9]   ACTION OF NITROGEN TRICHLORIDE ON PROTEINS - PROGRESS IN THE ISOLATION OF THE TOXIC FACTOR [J].
BENTLEY, HR ;
MCDERMOTT, EE ;
PACE, J ;
WHITEHEAD, JK ;
MORAN, T .
NATURE, 1949, 163 (4148) :675-676
[10]   TOXIC FACTOR FROM AGENIZED PROTEINS - METHIONINE AS THE ESSENTIAL REACTANT [J].
BENTLEY, HR ;
MCDERMOTT, EE ;
PACE, J ;
WHITEHEAD, JK ;
MORAN, T .
NATURE, 1950, 165 (4187) :150-151