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Synlett 2020; 31(17): 1649-1655
DOI: 10.1055/s-0040-1707172
DOI: 10.1055/s-0040-1707172
synpacts
Isoprene: A Promising Coupling Partner in C–H Functionalizations
We are grateful for financial support from the Dalian Institute of Chemical Physics, Dalian Outstanding Young Scientific Talent, and the National Natural Science Foundation of China (21702204, 21801239).Further Information
Publication History
Received: 12 May 2020
Accepted after revision: 30 May 2020
Publication Date:
02 July 2020 (online)
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
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For selected examples for coupling dienes with electrophiles, see:
For selected examples for coupling dienes with nucleophiles, see: