Recyclable Heterogeneous Palladium-Catalyzed Carbonylative Cyclization of 2-Iodoanilines with Aryl Iodides Leading to 2-Arylbenzoxazinones

Zhaotao Xu; Bin Huang; Zebiao Zhou; Mingzhong Cai

doi:10.1055/s-0039-1690265

Synthesis, Inhaltsverzeichnis

Synthesis 2020; 52(04): 581-590
DOI: 10.1055/s-0039-1690265

paper

Recyclable Heterogeneous Palladium-Catalyzed Carbonylative Cyclization of 2-Iodoanilines with Aryl Iodides Leading to 2-Arylbenzoxazinones

Zhaotao Xu

,

Bin Huang

,

Zebiao Zhou

,

Mingzhong Cai ∗

Key Laboratory of Functional Small Organic Molecules, Ministry of Education and College of Chemistry & Chemical Engineering, Jiangxi Normal University, Nanchang 330022, P. R. of China eMail: mzcai@jxnu.edu.cn

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Abstract

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Abstract

A highly efficient and practical heterogeneous palladium-catalyzed carbonylative coupling of 2-iodoanilines with aryl iodides has been developed. The reaction occurs smoothly in toluene at 110 °C with N,N-diisopropylethylamine as base under carbon monoxide (5 bar) and offers a general and powerful tool for the construction of various valuable 2-arylbenzoxazinones with excellent atom-economy, high functional group tolerance, good to high yields, and easy recyclability of the palladium catalyst. The reaction is the first example of heterogeneous palladium-catalyzed carbonylative coupling for the preparation of diverse 2-arylbenzoxazinones from commercially easily available 2-iodoanilines and aryl iodides.

Key words

palladium - benzoxazinone - carbonylative coupling - 2-iodoaniline - heterogeneous catalysis

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