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Base‐Promoted Aerobic Oxidation/Homolytic Aromatic Substitution Cascade toward the Synthesis of Phenanthridines
Author(s) -
Maiti Debabrata,
Halder Atreyee,
De Sarkar Suman
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201900995
Subject(s) - chemistry , homolysis , phenanthridine , dehydrogenation , cascade reaction , electrophilic aromatic substitution , yield (engineering) , nucleophilic aromatic substitution , medicinal chemistry , organic chemistry , photochemistry , combinatorial chemistry , radical , catalysis , nucleophilic substitution , materials science , metallurgy
The current protocol represents a transition metal‐free synthesis of polysubstituted phenanthridines from abundant starting materials like benzhydrol and 2‐iodoaniline derivatives. The reaction involves sequential oxidation of alcohol and direct condensation reaction with the amine resulting in a C−N bond formation followed by a radical C−C coupling in a cascade sequence. The used base potassium tert ‐butoxide plays a dual role in dehydrogenation and homolytic aromatic substitution reaction. Using this methodology, twenty substituted phenanthridine derivatives were synthesized with up to 85% isolated yield.