Synthesis of N-Imidoyl and N-Oxoimidoyl Sulfoximines from 1-Alkynes, N-Sulfonyl Azides, and Sulfoximines

Abstract

N-Imidoylation of sulfoximines is developed from a Cu-catalyzed three-component reaction from 1-alkynes, N-sulfonyl azides, and sulfoximines in THF at room temperature under air. In addition, N-oxoimidoylation of sulfoximines is accessed from a Cu-catalyzed three-component reaction from 1-alkynes, N-sulfonyl azides, and sulfoximines in THF at room temperature followed by a Cu-catalyzed oxidative reaction at 50 °C under air, producing N-oxoimidoyl sulfoximines.

CuI/I2‐Mediated Intramolecular Oxidative Cyclization Reaction of N‐(2‐pyridyl)amidines by the Direct Double C−H Functionalization of a C(sp3)−H Bond

“…Delightedly, an investigation found that N ‐(2‐pyridyl)amidines could be afforded by the efficient reaction between 2‐aminopyridines, terminal alkynes, and sulfonyl azides by using a copper salt and base. The reaction operated through ketenimine intermediates, and the transformation has been extensively reported by Chang,– Wang, Lee, Wu, Yi and their respective co‐workers under extremely mild conditions. However, to our surprise, according to Chang's procedure, in addition to a complex unidentified product, the desired 2‐amino analogs ( A ) from N ‐(2‐pyridyl)amidines were not observed under the same conditions.…”

Recent Advances in Multicomponent Reactions with Organic and Inorganic Sulfur Compounds

“…Lee and co‐workers recorded Cu‐catalyzed three‐component reaction from 1‐alkynes, N‐sulfonyl azides, and sulfoximines in THF at room temperature under air to synthesize the N‐oxoimidoylation of sulfoximines 140 (Scheme 35). [82] The advantages are that atomic economy, multiple‐bond‐forming efficiency, the utilization of readily available and environmentally benign reactants (Scheme 36).…”

N−H and C−H Functionalization of Sulfoximine: Recent Advancement and Prospects

“…In 2015, Lee and co‐workers ingeniously designed a Cu(I) catalyzed multi‐component reaction of terminal alkynes, sulfonyl azides and free‐ NH sulfoximines for the construction of N ‐imidoylation of sulfoximine 37 under aerobic conditions (Scheme 60). [78] Screening of metal catalysts such as CuCl, CuBr and CuI conclusively led to the use of CuI (10 mol %) as the most promising catalyst, whereas Et 3 N/THF were found to be the most suitable base and solvent. The methodology offered several notable features such as operational handiness, mild reaction conditions, exceptional functional group tolerance, rapid reaction and elimination of any oxidant/ligand.…”