Facile Preparation of Vinyl S‐Trifluoromethyl NH Aryl Sulfoximines

Abstract

We report herein the preparation of ortho‐vinylaryl S‐trifluoromethylated sulfoximines through cross‐coupling reactions. Two efficient palladium‐catalyzed procedures (Stille and Suzuki) were developed, with use of ortho‐iodo aryl sulfoximines as substrates, to give various vinyl derivatives in good yields. The difference in reactivity of the fluorinated derivatives, compared to nonfluorinated counterparts, allowed the use of free NH sulfoximines in the coupling processes, where they proved to be inert to cyclization. Finally, further transformations have been explored, such as metathesis coupling reactions, after post‐functionalization of the nitrogen atom by another vinyl group.

Divergent Synthesis of 1,2-Benzo[e]thiazine and Benzo[d]thiazole Analogues Containing a S-Trifluoromethyl Sulfoximine Group: Preparation and New Properties of the Adachi Reagent

“…1,141.7,139.4,137.6,137.1,131.8,129.9,129.8,129.6,128.9,127.2,126.9,121.7 (q,J = 332.7 Hz),111.0,105.1,20.4 5,147.3,141.3,137.2,129.7,129.3,128.7,127.7,126.6,126.5,120.8 (q,J = 332.8 Hz) 141.2,135.7,127.7,126.8,126.6,120.7 (q,J = 332.9 Hz). 8,141.6,137.5,129.1,128.1,127.2,121.5 (q,J = 332.3 Hz),120.8,111.0,102.9,37.3,24.4,16.6 4,141.2,135.7,127.1,126.8,126.5,120.7 (q,J = 333.5 Hz), 110.2 (q, J = 1.1 Hz), 100. 9,37.1,…”

“…The regioselectivity of the hydroamination also appeared to be dependent on the solvent. Triflic acid was identified as the best reagent to favor the formation of compound 4a (entries 1-4) and silver trifluoroacetate for the sulfoximine 5a (entries [5][6][7][8]. The structures 4a and 5a were determined by X-ray diffraction analysis (see ESI).…”

“…We recently reported the preparation of o -vinylaryl S -trifluoromethylated sulfoximines via Stille and Suzuki cross-coupling reactions, starting from iodo aryl sulfoximines . The obtained compounds proved to be stable, and no further cyclization occurred between the nitrogen and the double bonds.…”

Synergistic approach to polycycles through Suzuki–Miyaura cross coupling and metathesis as key steps

“…In another event, Magnier and co-workers [ 40 ] described a simple synthetic route to sulfoximines by adopting SM coupling and RCM as key steps. In this respect, SM coupling of sulfoximine 65 with potassium vinyltrifluoroborate ( 66 ) in the presence of a palladium catalyst produced vinyl sulfoximine derivative 67 (73%).…”

Design, Synthesis, and Antifungal Activity of Sulfoximine Derivatives Containing Nitroguanidine Moieties

“…Since the report that methionine sulfoximine could act as the toxic agent for canine hysteria (Figure 1), [8] sulfoximine derivatives have been widely concerned in medicinal chemistry. [9][10][11] Along with the development of synthetic methodology, sulfoximines can be easily modified and optimized at the nitrogen atom and sulfur fragment. Not surprisingly, various of derivatives bearing diverse biological activities have been discovered.…”