A palladium-catalyzed Heck/[4 + 1] decarboxylative cyclization cascade to access diverse heteropolycycles by using α-bromoacrylic acids as C1 insertion units

Literature Information

Publication Date 2021-08-09
DOI 10.1039/D1QO00861G
Impact Factor 5.281
Authors

Minghao Zhang, Fengru Zhou, Xinyu Xuchen, Liwei Zhou, Guobo Deng, Yun Liang, Yuan Yang


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Abstract

A novel palladium-catalyzed Heck/[4 + 1] decarboxylative cyclization cascade of alkene-tethered aryl iodides with α-bromoacrylic acids is reported. This strategy employs α-bromoacrylic acids as a new C1 synthon to assemble diverse heteropolycycles, such as cyclopenta[de]isoquinolinediones and cyclopenta[de]indolo[2,1-a]isoquinolinones, in moderate to excellent yields. This reaction enables the construction of three C–C bonds via sequential fused palladacycle formation, C(vinyl)–Br bond activation and decarboxylation.

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Organic Chemistry Frontiers

Organic Chemistry Frontiers
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Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

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