A concise synthetic strategy to alkynyl sulfides via transition-metal-free catalyzed C–S coupling of 1,1-dibromo-1-alkenes with thiophenols

A Route to Alkynyl Sulfides and Asymmetric Disulfides from Sodium Arylsulfiniate

“…GC-MS (EI) m/z: 244. (4-氟苯基)(苯乙炔基)硫醚(3h) [16] 26, 133.21, 130.68, 129.07, 127.64, 127.41, 121.89, 117.46, 111.42, 110.61, 97.29, 74.32, 54.33; GC-MS (EI) m/z: 240.…”

“…(苯乙炔基)(4-三氟甲基苯基)硫醚(3j) [16] 137.39,130.92,128.12,127.71,127.53,125.53,125.08,124.79,123.36 (q,J＝271.3 Hz,1C),121.38,98.48,72.56;19 F NMR (470 MHz, CDCl 3 ) δ: -62.40; GC-MS (EI) m/z: 278.…”

Synthesis of 2‐Organylchalcogenyl–benzo[b]selenophenes: 1‐(2,2‐Dibromovinyl)‐2‐butylselenanylbenzenes as Precursors to Access Alkynes Susceptible to Cyclization

“…On the other hand, 1,1‐dibromoalkenes are a versatile building block in organic synthesis, widely applied in coupling reactions for the preparation of a variety of molecules . Recently, Ni and co‐workers described the reaction of 1,1‐dibromoalkenes with several thiols in a basic media to afford selectively sulfanyl alkynes in good yields. More recently, we described the synthesis of ( E )‐1‐bromo‐1‐selenanylalkenes and ketene selenanylacetals, and ( E )‐bromostyrenes starting from 1,1‐dibromoalkenes.…”

Dual Role of Alkynyl Bromides in One-Step Synthesis of Bromo-Substituted Alkynyl Sulfides

“…[9] To overcome this drawback, researchers developed a transition-metal-free synthesis of alkynyl sulfides from 1,1-dibromo-1-alkenes with thiophenols. [10] However, low efficiency of the reaction is a major drawback. Recently, Frei and Waser successfully developed a highly chemoselective and practical thio-alkynylation reaction utilizing the hypervalent iodine alkyne transfer reagent triisopropylsilyl (TIPS) ethynyl benziodoxolone, [11] but the difficult accessibility of alkynation reagents limited the practical application of this method.…”