PPh₃O as an Activating Reagent for One-Pot Stereoselective Syntheses of Di- and Polybrominated Esters from Simple Aldehydes

Tian-Yang Yu, Hao Wei, Yong-Chun Luo, Yao Wang, Zhu-Yin Wang and Peng-Fei Xu*

*State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. China, Email: xupflzu.edu.cn

T.-Y. Hu, H. Wei, Y.-C. Luo, Y. Wang, Z.-Y. Wang, P.-F. Xu, J. Org. Chem., 2016, 81, 2730-2736.

DOI: 10.1021/acs.joc.5b02618

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Abstract

In an efficient one-pot method for the syntheses of di- and polybrominated esters from readily available aldehydes starting with a Wittig reaction, the in situ generated byproduct PPh₃O mediates a subsequent bromination with oxalyl bromide and greatly improves the efficiency of the cascade reaction.

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Key Words

Wittig reaction, 1,2-dibromoalkanes

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ID: J42-Y2016