Copper-catalyzed direct sulfenoamination of saturated ketones via in situ formed enaminones

Abstract

A sequential and efficient protocol for the synthesis of α-thiolated enaminones has been developed under copper-TEMPO systems. This reaction features a broad substrate scope to obtain the desired product in...

Selective Synthesis of Sulfonamides and Sulfenamides from Sodium Sulfinates and Amines

“…1 H NMR (400 MHz, CDCl 3 ): δ (ppm): 7.28−7.26 (m, 2H), 7.11−7.08 (m, 2H), 3.14 (t, J = 8.0 Hz, 4H), 2.61 (t, J = 8.0 Hz, 4H), 2.28 (s, 3H). 13 30 According to TP2, the target product 6g (90 mg, 73%) was synthesized as a colorless oil and purified by column chromatography (ethyl acetate/ petroleum ether = 1:5). 1 H NMR (400 MHz, CDCl 3 ): δ (ppm): 7.26−721 (m, 4H), 3.18 (t, J = 8.0 Hz, 4H), 2.61 (t, J = 8.0 Hz, 4H).…”

Highly Selective C–N and C–S Dual Functionalization of 1,3-Dicarbonyl Derivatives Using TBHP as an Oxidant

“…Recently in 2023, An et al studied the EDOT-COP photocatalyzed oxidative coupling of benzylamines to synthesize SCN in olefins and indoles . Furthermore, copper-catalyzed and electrosynthetic methods are also reported for the direct amino-thiolation. , (Figure ) Despite the notable progress that was made in the field to achieve amino-thiocyanation, reports on direct amino-thiocyanation remain unachievable via simple synthetic and inexpensive methods. Herein, we have developed a simple and direct protocol for the synthesis of ( E )-3-amino-2-thiocyanato-α,β-unsaturated carbonyl compounds (Figure ) without using an expensive metal/photocatalyst or electrolysis process.…”

Regio- and stereo-selective synthesis of β-phenylthio enamides via intramolecular 1,2-thiol migration

“…14 In this regard, the introduction of novel groups into sulfur-containing motifs might be an efficient way to develop new material molecules with unique functions and properties. Inspired by the recent studies of sulfur-mediated rearrangement reactions 15 and our continuous interest in the transformation of thiophenols, 16 herein we propose a unique Ritter-type reaction, which features the regio- and stereo-selective synthesis of β-phenylthio enamides via intramolecular 1,2-thiol migration (Scheme 1f).…”