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

被引：18
|
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
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