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Synthesis 2020; 52(04): 581-590
DOI: 10.1055/s-0039-1690265
DOI: 10.1055/s-0039-1690265
paper
Recyclable Heterogeneous Palladium-Catalyzed Carbonylative Cyclization of 2-Iodoanilines with Aryl Iodides Leading to 2-Arylbenzoxazinones
We thank the National Natural Science Foundation of China (No. 21462021), the Natural Science Foundation of Jiangxi Province of China (No. 20161BAB203086), and Key Laboratory of Functional Small Organic Molecule, Ministry of Education (No. KLFS-KF-201704) for financial support.Further Information
Publication History
Received: 01 September 2019
Accepted after revision: 22 October 2019
Publication Date:
13 November 2019 (online)
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 catalysisSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690265.
- Supporting Information
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