Remote difunctionalization of 2H-indazoles using Koser's reagents

被引:18
作者
Bhattacharjee, Suvam [1 ]
Laru, Sudip [1 ]
Hajra, Alakananda [1 ]
机构
[1] Visva Bharati, Dept Chem, Santini Ketan 731235, W Bengal, India
关键词
N BOND FORMATION; C-H BOND; HYPERVALENT IODINE; FUNCTIONALIZATION; CYCLIZATION; CHEMISTRY; PYRAZOLES;
D O I
10.1039/d1cc06129a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new, efficient, and metal-free protocol has been developed for remote difunctionalization of unreactive C-H bonds at the benzene core of 2H-indazole by employing Koser's reagents, which act as both sulfonyloxylating and iodinating agents under ambient air. The present methodology represents facile access to C-4-sulfonyloxylated and C-7-iodinated 2H-indazole derivatives with high regioselectivity, wide functional group tolerance, and broad substrate scope in good to excellent yields. The formed 4,7 disubstituted 2H-indazoles are the precursors of various C-4,7-functionalized 2H-indazoles through simple transformations.
引用
收藏
页码:981 / 984
页数:4
相关论文
共 43 条
[21]   Synthesis of a Range of Iodine(III) Compounds Directly from Iodoarenes [J].
Merritt, Eleanor A. ;
Olofsson, Berit .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (20-21) :3690-3694
[22]   Diaryliodonium Salts: A Journey from Obscurity to Fame [J].
Merritt, Eleanor A. ;
Olofsson, Berit .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (48) :9052-9070
[23]   Copper(I)-Catalyzed (Z)-β-(Tosyloxy)alkenyl Iodide Synthesis from (Aryl)[(E)-β-(tosyloxy)alkenyl]iodonium Tosylates: Diversity-Oriented Synthesis of Trisubstituted Alkenes [J].
Mondal, Keshab ;
Pan, Subhas Chandra .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (10) :2129-2132
[24]   Recent Achievements in the Rhodium-Catalyzed Concise Construction of Medium N-Heterocycles, Azepines and Azocines [J].
Ouyang, Wensen ;
Rao, Jianhang ;
Li, Yibiao ;
Liu, Xiaohang ;
Huo, Yanping ;
Chen, Qian ;
Li, Xianwei .
ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (24) :5576-5600
[25]   3-Aryliodonio-1,4-naphthoquinone-2-imides: A new class of aryliodonium 1,4 dipoles [J].
Papoutsis, I ;
Spyroudis, S ;
Varvoglis, A .
TETRAHEDRON LETTERS, 1996, 37 (06) :913-916
[26]   Hypervalent iodine(III) catalyzed oxidative C-N bond formation in water: synthesis of benzimidazole-fused heterocycles [J].
Rao, D. Nageswar ;
Rasheed, Sk ;
Vishwakarma, Ram A. ;
Das, Parthasarathi .
RSC ADVANCES, 2014, 4 (49) :25600-25604
[27]   Synthesis, Antiprotozoal Activity, and Cheminformatic Analysis of 2-Phenyl-2H-Indazole Derivatives [J].
Rodriguez-Villar, Karen ;
Yepez-Mulia, Lilian ;
Cortes-Gines, Miguel ;
Aguilera-Perdomo, Jacobo David ;
Quintana-Salazar, Edgar A. ;
Olascoaga Del Angel, Kevin Samael ;
Cortes-Benitez, Francisco ;
Palacios-Espinosa, Juan Francisco ;
Soria-Arteche, Olivia ;
Perez-Villanueva, Jaime .
MOLECULES, 2021, 26 (08)
[28]   Palladium-Catalyzed Cross-Coupling: A Historical Contextual Perspective to the 2010 Nobel Prize [J].
Seechurn, Carin C. C. Johansson ;
Kitching, Matthew O. ;
Colacot, Thomas J. ;
Snieckus, Victor .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (21) :5062-5085
[29]   Toolbox for Distal C-H Bond Functionalizations in Organic Molecules [J].
Sinha, Soumya Kumar ;
Guin, Srimanta ;
Maiti, Sudip ;
Biswas, Jyoti Prasad ;
Porey, Sandip ;
Maiti, Debabrata .
CHEMICAL REVIEWS, 2022, 122 (06) :5682-5841
[30]   sp3 Bis-Organometallic Reagents via Catalytic 1,1-Difunctionalization of Unactivated Olefins [J].
Sun, Shang-Zheng ;
Talavera, Laura ;
Spiess, Philipp ;
Day, Craig S. ;
Martin, Ruben .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (21) :11740-11744