@article {49366,
	title = {Iron-catalyzed C-C and C-N bond-forming tandem amidation offering access to 3-amino-3-aminomethyl-2-oxindole frameworks},
	journal = {Advanced Synthesis \& Catalysis},
	volume = {366},
	year = {2024},
	month = {JUN },
	pages = {2801-2810},
	type = {Article},
	abstract = {<p>
	An iron-catalyzed protocol for the synthesis of 3-amino-3-aminomethyl-2-oxindole heterocyclic structures is disclosed employing isatins and non-nucleophilic N-methoxybenzamides. This reaction class is associated with broad scope and tolerates numerous functionalities, such as fluoro, chloro, bromo, iodo, trifluoromethyl, nitrile, ester, ether, and alkenyl, including heteroaryl - thiophene, benzothiophene, carbazolyl, indolyl, eugenol, and polycyclic cholesterol moieties. Detailed mechanistic investigations reveal that the reaction proceeds via iron-catalyzed N-O bond cleavage in N-methoxybenzamides, generating formaldehyde and benzamide, and through the intermediacy of isatin-ketimines and N-(hydroxymethyl)benzamides. Overall, this amidation reaction involves one C-C and two C-N bond-forming tandem processes, providing a range of beta-amino-aminomethyl-oxindoles (45 examples) in up to 88\% yields. image</p>
},
	keywords = {benzamide, iron, Isatin, tandem amidation, tetrasubstituted carbon stereocenter},
	issn = {1615-4150},
	doi = {10.1002/adsc.202400216},
	author = {Ankade, Shidheshwar B. and Pradhan, Chandini and Samal, Pragnya Paramita and Gonnade, Rajesh G. and Krishnamurty, Sailaja and Punji, Benudhar}
}
