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Synthesis 2022; 54(03): 788-796
DOI: 10.1055/a-1647-5978
DOI: 10.1055/a-1647-5978
paper
Palladium-Catalyzed Cross-Coupling of 4-(Tosyloxy)quinazolines with H-Phosphonates and Phosphine Oxides: An Efficient Access to 2-(Hetero)aryl-4-phosphorylated Quinazolines
Financial support from the National Natural Science Foundation of China (no. 21762020), the Science Foundation of the Education Department of Jiangxi Province (no. GJJ161073), and the Key Laboratory of Functional Small Organic Molecules, Ministry of Education, Jiangxi Normal University (no. KLFS-KF-201408) is gratefully acknowledged.
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Abstract
A series of 2-(hetero)aryl-4-phosphorylated quinazolines was successfully synthesized in moderate to excellent yields via a palladium-catalyzed C–O/P–H cross-coupling reaction of 4-(tosyloxy)quinazolines with H-phosphonates and phosphine oxides. This efficient and green methodology provides an alternative straightforward protocol for the introduction of phosphorus groups to quinazoline compounds at the C4 position via C–O activation.
Key words
palladium catalysis - 4-(tosyloxy)quinazoline - H-phosphonates - phosphine oxides - 4-phosphorylated quinazolines - cross-couplingSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1647-5978.
- Supporting Information
Publication History
Received: 18 July 2021
Accepted after revision: 17 September 2021
Accepted Manuscript online:
17 September 2021
Article published online:
25 October 2021
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