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

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