Palladium-Catalyzed Denitrative α-Arylation of Heteroarenes with Nitroarenes via C-H and C-NO2 Bond Activations

被引:7
作者
Yao, Jiaxin [1 ]
Xiao, Yuxuan [1 ]
Li, Haiyan [1 ]
Yang, Xun [1 ]
Du, Jiahui [1 ]
Yin, Ying [1 ]
Feng, Lin [1 ]
Duan, Wengui [1 ]
Yu, Lin [1 ]
机构
[1] Guangxi Univ, Key Lab Appl Chem Technol & Resource Dev, Guangxi Coll & Univ, Sch Chem & Chem Engn, Nanning 530004, Guangxi, Peoples R China
关键词
ARYL; FUNCTIONALIZATION; (HETERO)ARENES; LIGAND; MILD;
D O I
10.1021/acs.orglett.4c02340
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A general approach for the alpha-arylation of heteroarenes with nitroarenes via denitrative coupling is reported for the first time. Various heteroarenes, including derivatives of furan, benzofuran, pyrrole, indole, thiophene, and benzothiophene, can be arylated at the alpha-position in moderate to good yields. Mechanistic studies demonstrate that the reaction proceeds via a CMD pathway, with C-H bond activation as the rate-determining step. Furthermore, the scalability and applicability in the synthesis of a drug molecule exemplify the utility of this protocol.
引用
收藏
页码:7307 / 7312
页数:6
相关论文
共 48 条
[1]   Sustainable protocols for direct C-H bond arylation of (hetero)arenes [J].
Albano, Gianluigi ;
Punzi, Angela ;
Capozzi, Maria Annunziata M. ;
Farinola, Gianluca M. .
GREEN CHEMISTRY, 2022, 24 (05) :1809-1894
[2]   Pd-Catalyzed Denitrative Intramolecular C-H Arylation [J].
Asahara, Kitty K. ;
Okita, Toshimasa ;
Saito, Ami N. ;
Muto, Kei ;
Nakao, Yoshiaki ;
Yamaguchi, Junichiro .
ORGANIC LETTERS, 2019, 21 (12) :4721-4724
[3]   Facile access to nitroarenes and nitroheteroarenes using N-nitrosaccharin [J].
Calvo, Roxan ;
Zhang, Kun ;
Passera, Alessandro ;
Katayev, Dmitry .
NATURE COMMUNICATIONS, 2019, 10 (1)
[4]   Construction of Heterobiaryl Skeletons through Pd-Catalyzed Cross-Coupling of Nitroarenes and Heterocyclic Arylborononate Esters with a Sterically Demanding NHC Ligand [J].
Chen, Wei ;
Chen, Wanzhi ;
Liu, Miaochang ;
Wu, Huayue .
ORGANIC LETTERS, 2022, :6983-6987
[5]   Ag(I)-C-H Activation Enables Near-Room-Temperature Direct α-Arylation of Benzo[b]thiophenes [J].
Colletto, Chiara ;
Panigrahi, Adyasha ;
Fernandez-Casado, Jaime ;
Larrosa, Igor .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (30) :9638-9643
[6]   A palladium- catalyzed regiocontrollable hydroarylation reaction of allenamides with B2pin2/ H2O+ [J].
Cui, Jie ;
Meng, Long ;
Chi, Xiaochen ;
Liu, Qing ;
Zhao, Pingping ;
Zhang, Dao-peng ;
Chen, Lei ;
Li, Xinjin ;
Dong, Yunhui ;
Liu, Hui .
CHEMICAL COMMUNICATIONS, 2019, 55 (30) :4355-4358
[7]   From Nature to Drug Discovery: The Indole Scaffold as a 'Privileged Structure' [J].
de Sa Alves, Fernando Rodrigues ;
Barreiro, Eliezer J. ;
Manssour Fraga, Carlos Alberto .
MINI-REVIEWS IN MEDICINAL CHEMISTRY, 2009, 9 (07) :782-793
[8]   A methylation platform of unconventional inert aryl electrophiles: trimethylboroxine as a universal methylating reagent [J].
Feng, Boya ;
Yang, Yudong ;
You, Jingsong .
CHEMICAL SCIENCE, 2020, 11 (23) :6031-6035
[9]   Palladium-catalyzed denitrative Sonogashira-type cross-coupling of nitrobenzenes with terminal alkynes [J].
Feng, Boya ;
Yang, Yudong ;
You, Jingsong .
CHEMICAL COMMUNICATIONS, 2020, 56 (05) :790-793
[10]   Palladium-catalyzed denitrative N-arylation of nitroarenes with pyrroles, indoles, and carbazoles [J].
Feng, Lin ;
Yao, Jiaxin ;
Yu, Lin ;
Duan, Wengui .
ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (09) :2351-2356