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Iron–Ligand Coordination in Tandem Radical Cyclizations: Synthesis of Benzo[ b ]thiophenes by a One‐pot Reaction of Iron 1,3‐Diketone Complexes with 2‐Thiosalicylic Acids
Author(s) -
Chan Sharon LaiFung,
Low KamHung,
Yang Chen,
Cheung Samantha HuiFung,
Che ChiMing
Publication year - 2011
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201100377
Subject(s) - chemistry , yield (engineering) , ligand (biochemistry) , tandem , diketone , radical cyclization , derivative (finance) , stereochemistry , pyridine , medicinal chemistry , combinatorial chemistry , receptor , biochemistry , materials science , economics , financial economics , metallurgy , composite material
Iron—the mediator : 1,3‐Diketone ligands coordinated to iron undergo unprecedented tandem reactions with 2‐thiosalicylic acids to give 2‐substituted 3‐hydroxylbenzo[ b ]thiophenes in up to 98 % yield. A similar reaction with 2‐mercaptonicotinic acid gave a thieno[2,3‐ b ]pyridine derivative in 72 % yield (see scheme). A mechanism involving redox transformation and tandem radical cyclization of the coordinated ligands is proposed.