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Synthesis 2021; 53(17): 3019-3028
DOI: 10.1055/a-1482-2567
DOI: 10.1055/a-1482-2567
special topic
Bond Activation – in Honor of Prof. Shinji Murai
Generation of Aryllithium Reagents from N-Arylpyrroles Using Lithium
This work was supported by the Japan Society for the Promotion of Science (JSPS KAKENHI Grant Number JP19H00895) as well as by JST Core Research for Evolutional Science and Technology (CREST Grant Number JPMJCR19R4). H.Y. also thanks The Asahi Glass Foundation for financial support.
Abstract
Treatment of 1-aryl-2,5-diphenylpyrroles with lithium powder in tetrahydrofuran at 0 °C results in the generation of the corresponding aryllithium reagents through reductive C–N bond cleavage.
Key words
organolithium reagents - C–N bond cleavage - lithium - pyrroles - metalation - reduction - deaminationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1482-2567.
- Supporting Information
Publication History
Received: 10 March 2021
Accepted after revision: 14 April 2021
Accepted Manuscript online:
14 April 2021
Article published online:
19 May 2021
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With sodium and potassium:
Alkali metal mediated cleavage of C–N bonds other than Ar–N bonds: