4.5 Article

A Metal-Free Approach for BrOnsted Acid Promoted C-H Alkylation of Heteroarenes with Alkyl Peroxides

Journal

SYNTHESIS-STUTTGART
Volume 50, Issue 16, Pages 3250-3256

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/s-0037-1609965

Keywords

metal-free conditions; BrOnsted acid; C-H alkylation; heteroarenes; alkyl peroxides

Funding

  1. NSFC [21502191, 21672213]
  2. Strategic Priority Research Program of the Chinese Academy of Sciences [XDB20000000]
  3. The 100 Talents Program
  4. The 1000 Youth Talents Program
  5. Natural Science Foundation of Fujian Province [2016J01081]
  6. Haixi Institute of CAS [CXZX-2017-P01]

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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 BrOnsted 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.

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