Silver(I)-Catalyzed Deprenylation of Allylsulfonamide Derivatives

Abstract

The silver(I)-catalyzed deprenylation of sulfonamide bearing prenyl functional groups on the nitrogen atom has been developed. In this reaction, the prenyl moiety was selectively eliminated without allyl or benzyl cleavage on the nitrogen atom. In addition, geranyl was also applicable for this elimination reaction. Furthermore, sulfonamide possessing two prenyl groups underwent a double deprenylation to form the corresponding deprenylated sulfonamide. Thus, a novel reactivity between the silver cation and double bond was observed.

Dehalogenative Deuteration of Unactivated Alkyl Halides Using D2O as the Deuterium Source

“…1 H NMR (400 MHz, CDCl 3 ): δ 7.77 (d, J = 8.0 Hz, 2H), 7.31 (d, J = 8.0 Hz, 2H), 5.76–5.66 (m, 1H), 5.18–5.14 (m, 1H), 5.09–5.06 (m, 2H), 3.59–3.55 (m, 2H), 2.42 (s, 3H); 13 C­{ 1 H} NMR (100 MHz, CDCl 3 ): δ 143.4, 136.8, 132.9, 129.6, 127.0, 117.5, 45.6, 21.4. The spectroscopic data are in agreement with that previously reported …”

Highly Selective and Catalytic C–N Bond Cleavage of Tertiary Sulfonamides: Scope and Mechanistic Insight

“…12 Solely, a single catalytic method, Ag I SbF 6mediated deprenylation of allylsulfonamides, has been reported at a very high temperature and under microwave-irradiated conditions. 13 Furthermore, a ruthenium-catalyzed C−N bond cleavage of N-propargyl sulfonamides and amides has also been reported. 14 Recently, an electrochemical method for C−N bond cleavage of secondary and tertiary N-alkyl sulfonamides has been developed.…”

Construction of 2,2-Dimethyloxepane Frameworks from Ene-Diols Catalyzed by Metal Catalyst or Brønsted Acid <i>via</i> 7-<i>Endo</i>-<i>Trig</i> Cyclization

“…Recently, we found that the Agcatalyst (AgSbF 6 ) worked with alkenes for the cycloisomerization and deprotection reaction. 24,25) Therefore, we next examined the AgSbF 6 -catalyzed 7-endo-trig cyclization of ene-diols. The results are shown in Table 3.…”