Pd-Catalyzed Sequential Arylation of 7-Azaindoles: Aggregate-Induced Emission of Tetra-Aryl 7-Azaindoles

被引：19
作者：
Cardoza, Savio [1 ]
Das, Parthasarathi [2 ]
Tandon, Vibha [1 ]
机构：
[1] Jawaharlal Nehru Univ, Special Ctr Mol Med, New Delhi 110067, India
[2] Indian Inst Technol, Indian Sch Mines, Dept Chem, Dhanbad 826004, Jharkhand, India
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 21期
关键词：
C-H ARYLATION; STATE PROTON-TRANSFER; DIRECT C-2 ARYLATION; PHOTOPHYSICAL PROPERTIES; INDOLES; DERIVATIVES; PYRROLES; ACCESS; SUBSTITUENTS; ALKYNYLATION;
D O I：
10.1021/acs.joc.9b02187
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Pd-catalyzed synthesis of multi-aryl 7-azaindoles using sequential arylation of 5-bromo-6-chloro-3-iodo-1-methyl-1H-pyrrolo[2,3-b] pyridine is established. Four diverse aryl groups are installed in a chemo-selective fashion providing a general method to synthesize sterically encumbered compounds and extended 7-azaindoles in 48-95% yields. Three-selective sequential arylations at C-3, C-5, and C-6 via Suzuki-Miyaura cross-coupling followed by direct C-2 arylation using a Pd catalyst and AgOTf as an additive are highlights of the present work. Interestingly, the tetra-aryl 7-azaindoles showed aggregate-induced emission (AIE) making it potentially useful as fluorophores in OLEDs, sensors, and bio-imaging tools.
引用
收藏
页码：14015 / 14029
页数：15
相关论文
共 86 条
[81]   Regiocontrolled Direct C-H Arylation of Indoles at the C4 and C5 Positions [J].
Yang, Youqing ;
Gao, Pan ;
Zhao, Yue ;
Shi, Zhuangzhi .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (14) :3966-3971
[82]   Palladium-Catalyzed C-H Arylation of Indoles at the C7 Position [J].
Yang, Youqing ;
Qiu, Xiaodong ;
Zhao, Yue ;
Mu, Yucheng ;
Shi, Zhuangzhi .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (02) :495-498
[83]   Cobalt(III)-Catalyzed C2-Selective C-H Alkynylation of Indoles [J].
Zhang, Zhuo-Zhuo ;
Liu, Bin ;
Wang, Cai-Yun ;
Shi, Bing-Feng .
ORGANIC LETTERS, 2015, 17 (16) :4094-4097
[84]   Furan Is Superior to Thiophene: A Furan-Cored AIEgen with Remarkable Chromism and OLED Performance [J].
Zhao, Zheng ;
Nie, Han ;
Ge, Congwu ;
Cai, Yuanjing ;
Xiong, Yu ;
Qi, Ji ;
Wu, Wenting ;
Kwok, Ryan T. K. ;
Gao, Xike ;
Qin, Anjun ;
Lam, Jacky W. Y. ;
Tang, Ben Zhong .
ADVANCED SCIENCE, 2017, 4 (08)
[85]   Aggregation-induced emission of siloles [J].
Zhao, Zujin ;
He, Bairong ;
Tang, Ben Zhong .
CHEMICAL SCIENCE, 2015, 6 (10) :5347-5365
[86]  
Zhu C., 2018, ACS APPL BIO MAT, V1, P1768
123456789