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Synthesis 2018; 50(16): 3250-3256
DOI: 10.1055/s-0037-1609965
DOI: 10.1055/s-0037-1609965
paper
A Metal-Free Approach for Brønsted Acid Promoted C–H Alkylation of Heteroarenes with Alkyl Peroxides
We thank NSFC (Grant Nos. 21502191 and 21672213), Strategic Priority Research Program of the Chinese Academy of Sciences (Grant No. XDB20000000), The 100 Talents Program, ‘The 1000 Youth Talents Program’, Natural Science Foundation of Fujian Province (Grant No. 2016J01081) and Haixi Institute of CAS (CXZX-2017-P01) for financial support.Further Information
Publication History
Received: 28 March 2018
Accepted after revision: 16 April 2018
Publication Date:
29 May 2018 (online)
Abstract
A metal-free protocol for Minisci C–H alkylation of heteroarenes using alkyl peroxides as the alkylating reagents and internal oxidants simultaneously under promotion of Brønsted acid has been demonstrated. A series of alkyl substituted heteroarenes were readily prepared by the C–H alkylation in moderate to good yields. A possible pathway involving the addition of alkyl radical to heterocycle followed by rearomatization is described.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1609965.
- Supporting Information
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Selected reviews on C–H functionalization:
Selected reviews on C–H alkylation:
Selected examples of Minisci reaction:
For selected reviews on the Minisci reaction, see:
Selected examples of metal-mediated Minisci-type C–H alkylation of heteroarenes:
Selected examples of photoredox Minisci-type C–H alkylation of heteroarenes via metal catalysis:
Selected examples of metal-free Minisci-type C–H alkylation of heteroarenes:
Our previous work on the decarboxylation of aliphatic acids:
Review: