Synthesis 2020; 52(04): 581-590
DOI: 10.1055/s-0039-1690265
paper
© Georg Thieme Verlag Stuttgart · New York

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

Zhaotao Xu
,
Bin Huang
,
Zebiao Zhou
,
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: [email protected]
› Author Affiliations
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.

Supporting Information

 
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