Isoprene: A Promising Coupling Partner in C–H Functionalizations

Wei-Song Zhang; Yan-Cheng Hu; Qing-An Chen

doi:10.1055/s-0040-1707172

Synlett, Table of Contents

Synlett 2020; 31(17): 1649-1655
DOI: 10.1055/s-0040-1707172

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Isoprene: A Promising Coupling Partner in C–H Functionalizations

Wei-Song Zhang

^aDalian Institute of Chemical Physics, Chinese Academy of Science, Dalian 116023, P. R. of China

^bUniversity of Chinese Academy of Sciences, Beijing 100049, P. R. of China Email: qachen@dicp.ac.cn

,

Yan-Cheng Hu

^aDalian Institute of Chemical Physics, Chinese Academy of Science, Dalian 116023, P. R. of China

,

Qing-An Chen∗

^aDalian Institute of Chemical Physics, Chinese Academy of Science, Dalian 116023, P. R. of China

› Author Affiliations

Abstract

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Abstract

Five-carbon dimethylallyl units, such as prenyl and reverse-prenyl, are widely distributed in natural indole alkaloids and terpenoids. In conventional methodologies, these valuable motifs are often derived from substrates bearing leaving groups, but these processes are accompanied by the generation of stoichiometric amounts of by-products. From an economical and environmental point of view, the basic industrial feedstock isoprene is an ideal alternative precursor. However, given that electronically unbiased isoprene might undergo six possible addition modes in the coupling reactions, it is difficult to control the selectivity. This article summarizes the strategies we have developed to achieve regioselective C–H functionalizations of isoprene under transition-metal and acid catalysis.

1 Introduction

2 Catalytic Coupling of Indoles with Isoprene

3 Catalytic Coupling of Formaldehyde, Arenes and Isoprene

4 Catalytic Coupling of 4-Hydroxycoumarins with Isoprene

5 Catalytic Coupling of Cyclic 1,3-Diketones with Isoprene

6 Conclusion and Outlook

Key words

isoprene - prenylation - C–H functionalization - regioselectivity - catalysis

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References

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