Palladium-Catalyzed Cross-Coupling of 4-(Tosyloxy)quinazolines with H-Phosphonates and Phosphine Oxides: An Efficient Access to 2-(Hetero)aryl-4-phosphorylated Quinazolines

Xinglin Ye; Jian Huang; Zhihong Deng; Yiyuan Peng

doi:10.1055/a-1647-5978

Synthesis, Table of Contents

Synthesis 2022; 54(03): 788-796
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

Xinglin Ye

^aDepartment of Chemistry and Environmental Engineering, Jiujiang University, Jiujiang, Jiangxi, 330025, P. R. of China

^bKey Laboratory for Green Chemistry of Jiangxi Province, Key Laboratory of Functional Small Molecules for Ministry of Education, Jiangxi Normal University, 99 Ziyang Avenue, Nanchang 330022, P. R. of China

,

Jian Huang

^bKey Laboratory for Green Chemistry of Jiangxi Province, Key Laboratory of Functional Small Molecules for Ministry of Education, Jiangxi Normal University, 99 Ziyang Avenue, Nanchang 330022, P. R. of China

,

Zhihong Deng

^bKey Laboratory for Green Chemistry of Jiangxi Province, Key Laboratory of Functional Small Molecules for Ministry of Education, Jiangxi Normal University, 99 Ziyang Avenue, Nanchang 330022, P. R. of China

,

Yiyuan Peng ∗

^bKey Laboratory for Green Chemistry of Jiangxi Province, Key Laboratory of Functional Small Molecules for Ministry of Education, Jiangxi Normal University, 99 Ziyang Avenue, Nanchang 330022, P. R. of China

› Author Affiliations

Abstract

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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-coupling

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References

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