4.7 Article

Di-tert Butyl Peroxide-Promoted Sequential Methylation and Intramolecular Aromatization of Isonitriles

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 356, Issue 16, Pages 3341-3346

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201400660

Keywords

C-H bond activation; domino reactions; 2-isocyanobiphenyls; methylation; phenanthridines

Funding

  1. National Natural Science Foundation of China [21272028, 21202013]
  2. Innovation & Entrepreneurship Talents Introduction Plan of Jiangsu Province
  3. Jiangsu Key Laboratory of Advanced Catalytic Materials Technology
  4. State Key Laboratory of Coordination Chemistry of Nanjing University
  5. Priority Academic Program Development of Jiangsu Higher Education Institutions

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The di-tert butyl peroxide (DTBP)-promoted sequential reaction of isonitriles is developed, leading to 6-methylphenanthridine derivatives in moderate to excellent yields. DTBP served as both promoter and methyl source. The procedure proceeds through the addition of a methyl radical derived from the peroxide to the isonitrile followed by aromatic homolytic cyclization. It tolerates a series of functional groups, such as fluoro, chloro, acetyl, methoxycarbonyl, cyano and trifluoromethyl.

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