Ni-Catalyzed dehydrogenative coupling of primary and secondary alcohols with methyl-N-heteroaromatics. Issue 22 (8th October 2018)

• Record Type: Journal Article
• Authors: Rana, Jagannath; Babu, Reshma; Subaramanian, Murugan; Balaraman, Ekambaram
• Is Part Of: Organic chemistry frontiers. Volume 5:Issue 22(2018)
• Page Start: 3250
• Page End: 3255
• Publication Date: 2018-10-08
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/c8qo00764k
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : Here we report the first base-metal catalyzed dehydrogenative coupling of primary (aromatic, heteroaromatic, and aliphatic) and secondary alcohols with methyl- N -heteroaromatics to form various C(sp 3 )-alkylated N -heteroaromatics. Abstract : Here we report the first base-metal catalyzed dehydrogenative coupling of primary (aromatic, heteroaromatic, and aliphatic) and secondary alcohols with methyl- N -heteroaromatics to form various C(sp 3 )-alkylated N -heteroaromatics. The reaction is enabled by Earth abundant, non-precious NiBr2 as a transition metal catalyst and N, N, N ′, N ′-tetramethylethylenediamine (TMEDA) as a ligand system. Mechanistic studies reveal that a hydrogen auto-transfer process is involved in the direct C(sp 3 )-alkylation and the reaction proceeds through an α-olefination process.