Hydrothiolation of terminal alkynes with diaryl disulfides and diphenyl diselenide: selective synthesis of (Z)-1-alkenyl sulfides and selenides

NaBH4/[bmim]BF4: a new reducing system to access vinyl selenides and tellurides

“…This regioselectivity is similar to that reported for the methods which use organic solvents. 1,[13][14][15][16][17][18][19][20] When the same protocol was applied to phenyl acetylene 1g, (E)-1,2-bis-phenylseleno styrene 5a was obtained in 85% yield after 3 h at 60 °C (Table 1, entry 7). This result is similar to that obtained under solvent-free conditions.…”

“…11,12 In this way, various methods are mentioned for the preparation of vinyl chalcogenides and the most common protocols involve the addition of organo chalcogenol, or the respective chalcogenolate anions, to terminal or internal alkynes. [1][2][3][4][5][6][7][8][9][10][13][14][15][16][17][18][19][20] On the other hand, ionic liquids (ILs) are receiving much attention in organic synthesis, both as recyclable solvents and/or catalysts. [21][22][23][24][25][26][27][28][29][30][31][32] Because product isolation or catalyst recycling is very easy in ILs and, in some cases, rate accelerations and/or selectivity improvements are also observed, they are regarded as environmentally friendly green solvents.…”

Hydroselenation and Carboselenation of Electron‐Deficient Alkynes with Isolable (Hydrido)(selenolato)platinum(II) Complexes and a Selenaplatinacycle Bearing a Triptycene Skeleton

“…(3) Similarly, the reaction of 3 with methyl propiolate was carried out in benzene at 60°C for 3 h to produce syn adduct (E)-9 in 36 % yield, together with [Pt(mp)(PPh 3 ) 2 ] (64 %), selenaplatinacycle 6 (24 %), and diselenide 8 (35 %) [Equation (4)]. In the 1 H NMR spectrum of (E)-9, a large coupling constant (16 Hz) between the two vinylic protons (δ = 5.43 and 6.27 ppm) indicated the trans stereochemistry.…”

“…Regioselective and/or stereoselective, transition-metalcatalyzed hydroselenation of terminal alkynes, [1][2][3] as well as other chalcogenation reactions of alkynes, [4][5][6] are important reactions that provide synthetically useful vinyl selenides [Equation (1)]. Carboselenation and carbothiolation [7] are also important synthetic reactions from the point of view of providing C-Se and C-C bonds in one step.…”

Na2S2O4‐Mediated Cyclocondensations of 2,2′‐Disulfanediyldi‐ anilines with Aldehydes: A Facile and Inexpensive Method for the Synthesis of 2‐Substituted Benzothiazoles

“…8 As a continuing interest in the application of rongalite in organic synthesis, we report herein a novel route to the synthesis of 2-substituted benzothiazole by cyclocondensation of 2,2'-disulfanediyldianiline with aldehydes in the presence of Na 2 S 2 O 4 and 4 Å molecular sieves under air (Eq. 1).…”