Categories: C-N Bond Formation >
Synthesis of imides
A convenient, efficient, and selective N-Alkylation of N-acidic heterocyclic compounds with alkyl halides is accomplished in ionic liquids in the presence of potassium hydroxide as a base. In this manner, phthalimide, indole, benzimidazole, and succinimide can be successfully alkylated.
Z.-G. Le, Z.-C. Chen, Y. Hu, Q.-G. Zheng, Synthesis, 2004, 208-212.
An efficient and simple method enables the N-alkylation of aromatic cyclic imides using cesium carbonate as the base in anhydrous N,N-dimethylformamide at low temperatures (20-70˚C). The employment of microwave irradiation presents noteworthy advantages over conventional heating. The method is compatible with base labile functional groups.
M. I. Escudero, L. D. Kremenchuzky, I. A. Perillo, H. Cerecetto, M. M. Blanco, Synthesis, 2011, 571-576.
In a one-pot cascade transformation of ketones into α-imidoketones, N-bromosuccinimide (NBS) provides both electrophilic bromine and nucleophilic nitrogen sources, and diazabicyclo[5.4.1]undec-7-ene (DBU) functions as a base and a nucleophilic promoter for the activation of NBS. α-Bromination is supposed as the key step in the process.
Y. Wei, S. Lin, F. Liang, Org. Lett., 2012, 14, 4202-4205.
An oxo-amination process with readily available N-bromosuccinimide (NBS) and secondary amines as N-sources and dimethyl sulfoxide (DMSO) as the oxidant provides amino alcohols in a single step. For the first time, the formation of reactive Me2S+-O-Br species generated by the interaction of NBS with DMSO has been proven.
P. K. Prasad, R. N. Reddi, A. Sudalai, Org. Lett., 2016, 18, 500-503.
In a palladium-catalyzed intermolecular aminocarbonylation of alkenes, the use of hypervalent iodine reagent can accelerate the reaction. The current transformation presents a convenient method to generate β-amino acid derivatives from simple alkenes.
J. Cheng, X. Qi, M. Li, P. Chen, G. Liu, J. Am. Chem. Soc., 2015, 137, 2480-2483.
AgBF4 or InBr3/AgBF4 (1:3) as catalyst and N-halophthalimide as both nitrogen and halogen source enable a simple, efficient, and highly atom economic haloamidation of simple alkenes. A broad range of olefins afford vicinal haloamines in good yields and with high regioselectivity and diastereoselectivity.
L. Song, S. Luo, J.-P. Cheng, Org. Lett., 2013, 15, 5702-5705.
TBAI as catalyst and TBHP as oxidant enable a metal-free cross-coupling of enamines and electron-deficient amines through oxidative C(sp2)-N bond formation. This efficient organocatalytic synthesis of synthetically useful diaminoalkene derivatives features readily available starting materials and wide substrate scope.
Y. Yuan, W. Hou, D. Zhang-Negrerie, K. Zhaou, Y. Du, Org. Lett., 2014, 16, 5410-5113.