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 | Zendy

Bisht Narendra | Zendy; Babu Srinivasarao Arulananda | Zendy; Tomar Radha | Zendy

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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.

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