α-Oxocarboxylic Acids as Three-Carbon Insertion Units for Palladium-Catalyzed Decarboxylative Cascade Synthesis of Diverse Fused Heteropolycycles

被引:39
作者
Zhou, Liwei [1 ]
Qiao, Shujia [1 ]
Zhou, Fengru [1 ]
Xuchen, Xinyu [1 ]
Deng, Guobo [1 ]
Yang, Yuan [1 ]
Liang, Yun [1 ]
机构
[1] Hunan Normal Univ, Natl & Local Joint Engn Lab New Petro Chem Mat &, Key Lab Chem Biol & Tradit Chinese Med Res,Minist, Key Lab Assembly & Applicat Organ Funct Mol Hunan, Changsha 410081, Hunan, Peoples R China
基金
中国国家自然科学基金;
关键词
C-H ACTIVATION; C(SP(2))-H BOND ACTIVATION; 2 ARYL HALIDES; EFFICIENT SYNTHESIS; FACILE APPROACH; DOMINO REACTION; KETO ACIDS; ACYLATION; FUNCTIONALIZATION; SPIROCYCLIZATION;
D O I
10.1021/acs.orglett.1c00493
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel palladium-catalyzed decarboxylative cascade cyclization for the assembly of diverse fused heteropolycycles by employing alpha-oxocarboxylic acids as three-carbon insertion units is reported. This protocol enables the synthesis of isoquinolinedione- and indolo[2,1-a]isoquinolinone-fused benzocycloheptanones in moderate to good yields by the use of different aryl iodides, including alkene-tethered 2-iodobenzamides and 2-(2-iodophenyl)-1H-indoles. Notably, the approach achieves simultaneous construction of both six- and seven-membered rings via sequential intramolecular carbopalladation, C-H activation, and decarboxylation.
引用
收藏
页码:2878 / 2883
页数:6
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