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- Title
Direct esterification of amides by the dimethylsulfate-mediated activation of amide C–N bonds.
- Authors
Qin, Hongjian; Han, Zijian; Bonku, Emmanuel Mintah; Sun, Haiguo; Odilov, Abdullajon; Zhu, Fuqiang; Abduahadi, Safomuddin; Zhu, Weiliang; Shen, Jingshan; Aisa, Haji A.
- Abstract
Amides are important intermediates in organic chemistry and the pharmaceutical industry, but their low reactivity requires catalysts and/or severe reaction conditions for esterification. Here, a novel approach was devised to convert amides into esters without the use of transition metals. The method effectively overcomes the inherent low reactivity of amides by employing dimethylsulfate-mediated reaction to activate the C-N bonds. To confirm the proposed reaction mechanism, control experiments and density functional theory (DFT) calculations were conducted. The method demonstrates a wide array of substrates, including amides with typical H/alkyl/aryl substitutions, N,N-disubstituted amides, amides derived from alkyl, aryl, or vinyl carboxylic acids, and even amino acid substrates with stereocentres. Furthermore, we have shown the effectiveness of dimethylsulfate in removing acyl protective groups in amino derivatives. This study presents a method that offers efficiency and cost-effectiveness in broadening the esterification capabilities of amides, thereby facilitating their increased utilization as synthetic compounds in diverse transformations. Amides are important intermediates in organic chemistry and the pharmaceutical industry, but their low reactivity requires catalysts and/or harsh reaction conditions to esterify them. Here, the authors report a versatile and mild dimethyl sulfate-mediated reaction to activate and esterify C—N bonds, achieving up to 95% amide bond cleavage.
- Subjects
AMIDES; CARBOXYLIC acids; SCISSION (Chemistry); ORGANIC chemistry; INTERMEDIATES (Chemistry); PHARMACEUTICAL chemistry; ESTERIFICATION; ACYL group
- Publication
Communications Chemistry, 2024, Vol 7, Issue 1, p1
- ISSN
2399-3669
- Publication type
Article
- DOI
10.1038/s42004-024-01180-9