Synthesis of sulfilimines

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A metal-free, sustainable, and efficient sulfur-selective alkylation of readily accessible sulfenamides with commercially available halogenated hydrocarbons under basic conditions provides sulfilimines in high yields and short reaction times.
G. Huang, X. Lu, K. Yang, X. Xu, Org. Lett., 2023, 25, 3173-3178.

Sulfur alkylation of N-acyl sulfenamides with alkyl halides provides sulfilimines in good yields. A broad scope was established with a variety of aryl and alkyl sulfenamides, including for different N-acyl groups. A proof-of-concept asymmetric phase-transfer alkylation was also demonstrated.
A. T. Champlin, J. A. Ellman, J. Org. Chem., 2023, 88, 7607-7614.

An efficient S-arylation of sulfenamides with diaryliodonium salts provides sulfilimines in excellent yields smoothly under transition-metal-free and aerobic conditions. This protocol is scalable and exhibits a broad substrate scope, good functional group tolerance, and excellent chemoselectivity.
X. Wu, Y. Li, M. Chen, F.-S. He, J. Wu, J. Org. Chem., 2023, 88, 9352-9359.

A transition-metal-free and redox-neutral S-arylation of sulfenamides with diaryliodonium salts provides sulfilimines in very good yields and with superlative chemoselectivity under exceptionally mild conditions.
G. Huang, X. Lu, F. Liang, Org. Lett., 2023, 25, 3179-3183.

A practical and efficient base-mediated sulfur arylation reaction of N-acyl and N-aryl sulfenamides with various diaryliodonium salts smoothly provides sulfilimines in high yields with excellent chemoselectivities.
Q. Zhou, J. Li, T. Wang, X. Yang, Org. Lett., 2023, 25, 4335-4339.

The reaction of sulfinimidate esters with Grignard reagents enables the preparation of protected sulfilimines in high yields and with a remarkable structural variability. Moreover, the transformation can be performed in cyclopentyl methyl ether as a green solvent.
M. Andresini, M. Spennachio, M. Colella, G. Losito, A. Aramini, L. Degennaro, R. Luisi, Org. Lett., 2021, 23, 6795-6800.

Sulfur-(hetero)arylation of sulfenamides with commercially abundant (hetero)aryl iodides by Ullmann-type coupling with inexpensive copper(I) iodide as the catalyst provides many bioactive high oxidation state sulfur compounds. Smiles rearrangement of electron-deficient S-heteroaryl sulfilimines is also disclosed.
N. S. Greenwood, J. A. Ellman, Org. Lett., 2023, 25, 4759-4764.

Sulfur-Arylation of Sulfenamides via Chan-Lam Coupling with Boronic Acids: Access to High Oxidation State Sulfur Pharmacophores
N. S. Greenwood, J. A. Ellman, Org. Lett., 2023, 25, 2830-2834.

A mild method enables the preparation of sulfilimines via selective S-C bond formation using readily available alkylation reagents such alkyl bromides or alkyl iodides and water as solvent. The method is easy to perform, and it is convenient for late-stage diversification of drugs.
Y. Chen, D.-m. Fang, H.-s. Huang, X.-k. Nie, S.-q. Zhang, X. Cui, Z. Tang, G.-x. Li, Org. Lett., 2023, 25, 2134-2138.

A facile and efficient multicomponent reaction of arynes, sulfamides, and thiosulfonates provides a broad range of sulfilimines in very good yields. This protocol could be conducted on a gram scale, and the products were easily converted to sulfides and sulfoximines. Mechanism studies revealed that a sulfenamide generated in situ is the key intermediate for the reaction.
P. Xie, Y. Zheng, Y. Luo, J. Luo, L. Wu, Z. Cai, L. He, Org. Lett., 2023, 25, 6133-6138.

A transition metal-free, selective S-arylation reaction between sulfenamides and arynes provides structurally diverse sulfilimines under mild and redox-neutral conditions in good yields. The application value of the method was further demonstrated by scale-up, downstream derivatization, and robustness screen.
Y. Guo, Z. Zhuang, X. Feng, Q. Ma, N. Li, C. Jin, H. Yoshida, J. Tan, Org. Lett., 2023, 25, 7192-7197.