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Synthesis of maleimides

Recent Literature

Depending on the temperature, a desulfitative arylation of maleimide provides both mono- and diaryl maleimides.
M. Abbasnia, M. Sheykhan, T. Ghaffari, E. Safari, J. Org. Chem., 2020, 85, 11688-11698.

Intermolecular [2 + 2 + 1] ruthenium-catalyzed cocyclization of isocyanates, alkynes, and CO proceeded smoothly in mesitylene at 130°C to give a variety of polysubstituted maleimides in excellent yields with high selectivity.
T. Kondo, M. Nomura, Y. Ura, K. Wada, T. Mitsudo, J. Am. Chem. Soc., 2006, 128, 14816-14817.

An efficient and convenient palladium-catalyzed cyclization reaction of alkynes with isocyanides followed by hydrolysis enables a practical synthesis of a broad range of valuable polysubstituted maleimide derivatives under mild reaction conditions. Isocyanide serve as both C and N sources.
W. Hu, J. Zheng, J. Li, B. Liu, W. Wu, H. Liu, H. Jiang, J. Org. Chem., 2016, 81, 12451-12458.

A palladium-catalyzed C-C bond activation of cyclopropenone and concomitant carbonylative amination provides maleimides. Eliminated carbon monoxide from the cyclopropenone is efficiently recaptured in the catalytic cycle for the formation of maleimides.
T. Nanda, P. C. Ravikumar, Org. Lett., 2020, 22, 1368-1374.

Unsymmetrical 3,4-disubstituted maleimides have been synthesized by palladium-catalyzed cross-coupling reactions of indium organometallics with 3,4-dihalomaleimides.Various alkyl, aryl, heteroaryl, and alkynyl 3,4-disubstituted maleimides have been prepared in good yields and with high selectivity.
L. Bouissane, J. P. Sestelo, L. A. Sarandeses, Org. Lett., 2009, 11, 1285-1288.

Unsymmetrical 3,4-disubstituted maleimides have been synthesized by palladium-catalyzed cross-coupling reactions of indium organometallics with 3,4-dihalomaleimides.Various alkyl, aryl, heteroaryl, and alkynyl 3,4-disubstituted maleimides have been prepared in good yields and with high selectivity.
L. Bouissane, J. P. Sestelo, L. A. Sarandeses, Org. Lett., 2009, 11, 1285-1288.

The use of secondary amines and NXS (X = Cl, Br, I) enables an unprecedented copper-catalyzed oxidative aminohalogenation of electron-deficient maleimides. This simple and green multicomponent reaction offers late-stage modification of drug molecules and in situ formation of N-iodoamines for efficient alkene aminoiodination.
X. Zhou, Y. Yao, C. Wang, Y. Xu, W. Zhang, Y. Ma, G. Wu, Org. Lett., 2021, 23, 3669-3673.

Triphenylphosphine catalyzes a coupling of maleimides with 1,3,5-triazinanes to provide 3-aminomethylated maleimides via a Morita-Baylis-Hillman (MBH) reaction.
W.-K. Wang, F.-Y. Bao, S.-T. Wang, S.-Y. Yao, J. Org. Chem., 2023, 88, 7483-7488.