Rhodium‐Catalyzed Decarbonylative Direct Olefination of Arenes with Vinyl Carboxylic Acids

Ruiying Qiu, Ling‐juan Zhang, Conghui Xu, Yixiao Pan, Hongze Pang, Lijin Xu, Huanrong Li

Advanced Synthesis & Catalysis · 2015 · 38 citations · 120 references

Concepts

Abstract

Abstract A rhodium(I)‐catalyzed direct CH bond olefination of pyridyl‐substituted arenes with readily available vinyl carboxylic acids has been realized. This reaction occurred efficiently without the need for any external oxidant, affording the ortho ‐olefinated products in high yields and excellent regioselectivities. Diversely substituted vinyl carboxylic acids behaved as efficient olefination reagents under the reaction conditions, and a range of functional groups in both coupling partners was well tolerated. Mechanistic studies indicated that a decarbonylation step is involved in this catalytic process, and pivalic anhydride [( t‐ BuCO) 2 O] acts as the activator of the carboxylic acids for the in situ generation of highly active anhydrides. magnified image

References

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