Palladium-Catalyzed Cascade Reactions of 2-(Cyanomethoxy)chalcones with Arylboronic Acids: Selective Synthesis of Emissive Benzofuro[2,3-c]pyridines

被引：35
作者：
Xiong, Wenzhang [1 ]
Hu, Kun [1 ]
Lei, Yunxiang [2 ]
Zhen, Qianqian [1 ]
Zhao, Zhiwei [1 ]
Shao, Yinlin [1 ]
Li, Renhao [3 ]
Zhang, Yetong [1 ]
Chen, Jiuxi [1 ]
机构：
[1] Wenzhou Univ, Coll Chem & Mat Engn, Wenzhou 325035, Peoples R China
[2] Beijing Inst Technol, Sch Mat Sci & Engn, Beijing 100081, Peoples R China
[3] Wenzhou Med Univ, Sch Pharmaceut Sci, Wenzhou 325035, Peoples R China
来源：
ORGANIC LETTERS | 2020年 / 22卷 / 04期
基金：
中国国家自然科学基金;
关键词：
AGGREGATION-INDUCED EMISSION; PD(II)/BIPYRIDINE-CATALYZED CONJUGATE ADDITION; ARYL KETONES; ALPHA; BETA-UNSATURATED KETONES; TANDEM REACTION; CONSTRUCTION; FLUORESCENCE; NITRILES; ENONES; RING;
D O I：
10.1021/acs.orglett.9b04185
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The Pd(II)-catalyzed cascade reactions of 2-(cyanomethoxy)chalcones with arylboronic acids were demonstrated, allowing the rapid construction of benzofuro[2,3-c]pyridine skeletons with excellent selectivity. These transformations involve the domino-style formation of C-C/C-C/C-N bonds through nitrile carbopalladation, intramolecular Michael addition, cyclization, and aromatization. This chemistry allows for the reactions of 2-(cyanomethoxy)-chalcones with thiophen-3-ylboronic acid, providing 3-aryl-1-(thiophen-3-yl)benzofuro[2,3-c]pyridines in moderate to good yields. In addition, the resulting products represent a new class of emissive fluorophores.
引用
收藏
页码：1239 / 1243
页数：5
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