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 | Zendy

Chan Sharon LaiFung | Zendy; Low KamHung | Zendy; Yang Chen | Zendy; Cheung Samantha HuiFung | Zendy; Che ChiMing | Zendy

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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.

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