7474-36-4Relevant articles and documents
Tandem Photoredox Catalysis: Enabling Carbonylative Amidation of Aryl and Alkylhalides
Connell, Timothy U.,Forni, José A.,Micic, Nenad,Polyzos, Anastasios,Weragoda, Geethika
supporting information, p. 18646 - 18654 (2020/08/21)
We report a new visible-light-mediated carbonylative amidation of aryl, heteroaryl, and alkyl halides. A tandem catalytic cycle of [Ir(ppy)2(dtb-bpy)]+ generates a potent iridium photoreductant through a second catalytic cycle in the presence of DIPEA, which productively engages aryl bromides, iodides, and even chlorides as well as primary, secondary, and tertiary alkyl iodides. The versatile in situ generated catalyst is compatible with aliphatic and aromatic amines, shows high functional-group tolerance, and enables the late-stage amidation of complex natural products.
Preparation method of fatty acid amide
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Paragraph 0052, (2019/02/13)
The invention relates to a preparation method of fatty acid amide. The method includes: adding hydroxylamine hydrochloride, a transition metal, a phosphine ligand, olefin and a solvent into a high pressure reaction kettle in order, carrying out hydroamine
Nickel-catalyzed transamidation of aliphatic amide derivatives
Dander, Jacob E.,Baker, Emma L.,Garg, Neil K.
, p. 6433 - 6438 (2017/08/29)
Transamidation, or the conversion of one amide to another, is a long-standing challenge in organic synthesis. Although notable progress has been made in the transamidation of primary amides, the transamidation of secondary amides has remained underdeveloped, especially when considering aliphatic substrates. Herein, we report a two-step approach to achieve the transamidation of secondary aliphatic amides, which relies on non-precious metal catalysis. The method involves initial Boc-functionalization of secondary amide substrates to weaken the amide C-N bond. Subsequent treatment with a nickel catalyst, in the presence of an appropriate amine coupling partner, then delivers the net transamidated products. The transformation proceeds in synthetically useful yields across a range of substrates. A series of competition experiments delineate selectivity patterns that should influence future synthetic design. Moreover, the transamidation of Boc-activated secondary amide derivatives bearing epimerizable stereocenters underscores the mildness and synthetic utility of this methodology. This study provides the most general solution to the classic problem of secondary amide transamidation reported to date.
