Ascorbic acid as an initiator for the direct C-H arylation of (hetero)arenes with anilines nitrosated in situ.
Ascorbic acid (vitamin C) has been used as a radical initiator in a metal-free direct C-H arylation of (hetero)arenes. Starting from an aniline, the corresponding arenediazonium ion is generated in situ and immediately reduced by vitamin C to an aryl radical that undergoes a homolytic aromatic substitution with a (hetero)arene. Notably, neither heating nor irradiation is required. This procedure is mild, operationally simple, and constitutes a greener approach to arylation.
Instituto de Productos Naturales y Agrobiología, CSIC, Francisco Sánchez, 3, 38206 La Laguna, Tenerife (Spain).
Fernando Pinacho
FP
Crisóstomo
Tomás
T
Martín
Romen
R
Carrillo
D000814:Aniline Compounds / Q000737:chemistry*; D001205:Ascorbic Acid / Q000737:chemistry*; D001555:Benzene Derivatives / Q000138:chemical synthesis / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry; D005609:Free Radicals / Q000737:chemistry; D055772:Green Chemistry Technology; D006859:Hydrogen / Q000737:chemistry
D000814:Aniline Compounds; D001555:Benzene Derivatives; D005609:Free Radicals; D002244:Carbon; D006859:Hydrogen; D001205:Ascorbic Acid; C023650:aniline
CH arylation; aromatic substitution; ascorbic acid; green chemistry; metal-free reactions