Metal-free Cross-Dehydrogenative Coupling for α-Arylation of 3-Aryloxindoles

被引:0
作者
Hu, Fangzhi [1 ,2 ,3 ]
Wang, Peng [2 ]
Li, Jiawei [2 ]
Dong, Fengying [2 ]
Jin, Long Yi [1 ]
Li, Shuai-Shuai [2 ]
机构
[1] Yanbian Univ, Natl Demonstrat Ctr Expt Chem Educ, Dept Chem, Yanji 133002, Peoples R China
[2] Qingdao Agr Univ, Coll Chem & Pharmaceut Sci, Qingdao 266109, Peoples R China
[3] Hangzhou Foster Pharmaceut Co LTD, Hangzhou 310000, Peoples R China
基金
中国国家自然科学基金;
关键词
quaternary carbon centers; cross-dehydrogenative coupling; 3,3-diaryloxindoles; metal-free; arylation; NATURAL-PRODUCTS; TERTIARY-AMINES; INDOLES; FUNCTIONALIZATION; REARRANGEMENT; CONSTRUCTION; DERIVATIVES; ALKYLATION; CHEMISTRY; OXINDOLES;
D O I
10.1002/asia.202500001
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The creation of quaternary carbon centers has been a formidable challenge in organic synthesis due to steric impediments, especially for the polyaryl substituted quaternary carbon centers. Up to now, a few of methods were reported for achieving the alpha-arylation of 3-aryloxindoles to construct 3,3-diaryloxindoles. We now asserted the TfOH-catalyzed cross-dehydrogenative coupling reaction between the tertiary C(sp3)-H and readily available arenes under air atmosphere in green reaction medium for rapid construction of 3,3-diaryloxindoles. In addition, the mechanism of the metal-free cross-dehydrogenative coupling with air as oxidant was meticulously explored.
引用
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页数:7
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共 56 条
[1]   New isatin derivatives with antioxidant activity [J].
Andreani, Aldo ;
Burnelli, Silvia ;
Granaiola, Massimiliano ;
Leoni, Alberto ;
Locatelli, Alessandra ;
Morigi, Rita ;
Rambaldi, Mirella ;
Varoli, Lucilla ;
Cremonini, Mauro Andrea ;
Placucci, Giuseppe ;
Cervellati, Rinaldo ;
Greco, Emanuela .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (04) :1374-1378
[2]   Isothiourea-Catalyzed Enantioselective Addition of 4-Nitrophenyl Esters to Iminium Ions [J].
Arokianathar, Jude N. ;
Frost, Aileen B. ;
Slawin, Alexandra M. Z. ;
Stead, Darren ;
Smith, Andrew D. .
ACS CATALYSIS, 2018, 8 (02) :1153-1160
[3]   Copper Catalyzed Oxidative Arylation of Tertiary Carbon Centers [J].
Basnet, Prakash ;
Sebold, Melissa B. ;
Hendrick, Charles E. ;
Kozlowski, Marisa C. .
ORGANIC LETTERS, 2020, 22 (24) :9524-9528
[4]   Enantioselective organocatalysis using SOMO activation [J].
Beeson, Teresa D. ;
Mastracchio, Anthony ;
Hong, Jun-Bae ;
Ashton, Kate ;
MacMillan, David W. C. .
SCIENCE, 2007, 316 (5824) :582-585
[5]   Synthetic Strategies toward Natural Products Containing Contiguous Stereogenic Quaternary Carbon Atoms [J].
Bueschleb, Martin ;
Dorich, Stephane ;
Hanessian, Stephen ;
Tao, Daniel ;
Schenthal, Kyle B. ;
Overman, Larry E. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (13) :4156-4186
[6]   Organocatalytic Synthesis of Spiro[pyrrolidin-3,3′-oxindoles] with High Enantiopurity and Structural Diversity [J].
Chen, Xiao-Hua ;
Wei, Qiang ;
Luo, Shi-Wei ;
Xiao, Han ;
Gong, Liu-Zhu .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (38) :13819-13825
[7]   Organocatalytic Enantioselective Synthesis of Atropisomeric Aryl-p-Quinones: Platform Molecules for Diversity-Oriented Synthesis of Biaryldiols [J].
Chen, Ye-Hui ;
Li, Heng-Hui ;
Zhang, Xiao ;
Xiang, Shao-Hua ;
Li, Shaoyu ;
Tan, Bin .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (28) :11374-11378
[8]   Research Progress on Construction of Heterocyclic Skeletons Based on α-Hydride Transfer Strategy [J].
Chen Yuzhuo ;
Sun Hongmei ;
Wang Liang ;
Hu Fangzhi ;
Li Shuaishuai .
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2023, 43 (07) :2323-2337
[9]   Synthesis and Antitumor Effect in Vitro and in Vivo of Substituted 1,3-Dihydroindole-2-ones [J].
Christensen, Mette K. ;
Erichsen, Kamille D. ;
Trojel-Hansen, Christina ;
Tjornelund, Jette ;
Nielsen, Soren J. ;
Frydenvang, Karla ;
Johansen, Tommy N. ;
Nielsen, Birgitte ;
Schested, Maxwell ;
Jensen, Peter B. ;
Ikaunieks, Martins ;
Zaichenko, Andrei ;
Loza, Einars ;
Kalvinsh, Ivars ;
Bjorkling, Fredrik .
JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (19) :7140-7145
[10]   Isoform-Specific Inhibition of Cyclophilins [J].
Daum, Sebastian ;
Schumann, Michael ;
Mathea, Sebastian ;
Aumueller, Tobias ;
Balsley, Molly A. ;
Constant, Stephanie L. ;
de Lacroix, Boris Feaux ;
Kruska, Fabian ;
Braun, Manfred ;
Schiene-Fischer, Cordelia .
BIOCHEMISTRY, 2009, 48 (26) :6268-6277