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Pd(II)‐Catalyzed, Bidentate Directing Group‐aided Alkylation of sp 3 γ‐C−H Bonds: Access to 3‐Alkylated Thiophene/Furan and Benzothiophene/Benzofuran Motifs
Author(s) -
Bisht Narendra,
Babu Srinivasarao Arulananda,
Tomar Radha
Publication year - 2020
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.202000284
Subject(s) - benzothiophene , benzofuran , chemistry , alkylation , furan , thiophene , denticity , organic chemistry , amination , medicinal chemistry , carboxylic acid , catalysis , combinatorial chemistry , crystal structure
We report the Pd(II)‐catalyzed bidentate directing group 8‐aminoquinoline‐aided sp 3 γ ‐C−H alkylation of 3‐methyl‐ thiophene/furan‐2‐carboxylic acid and 3‐methyl‐ benzothiophene/benzofuran‐2‐carboxylic acid systems. While the 8‐aminoquinoline‐aided sp 3 γ ‐C−H functionalization including arylation or amidation or amination of carboxylic acid derivatives are well known, however, the Pd(II)‐catalyzed bidentate directing group 8‐aminoquinoline‐aided sp 3 γ ‐C−H alkylation is not explored. Notably, 2‐ and/or 3‐alkylated thiophene/furan and benzothiophene/benzofuran motifs are found in pharmaceutically active molecules. Accordingly, this work reveals the scope of the 8‐aminoquinoline‐aided sp 3 γ ‐C−H alkylation method, and its usefulness by enriching the libraries of 3‐alkylated thiophene/furan and benzothiophene/benzofuran motifs.