Chalcogenoacetylenes Obtained by Indium(III) Catalysis: Dual Catalytic Activation of Diorgano Dichalcogenides and C_sp–H Bonds

Abstract

A new approach for the one-pot synthesis of alkynyl chalcogenides, exemplified mainly by selenides, was developed in which dual activation of diorgano dichalcogenides and terminal acetylenes is achieved by using an indium(III) catalyst.

Synthesis of Chalcogenoacetylenes from Diorgano Diselenides and Terminal Acetylenes employing Bi (III)

“…4 In this sense, commercially available diphenyl diselenide 1a (0.5 mmol), phenylacetylene 2a (1.0 mmol), bismuth catalysts (10 mol%), KI (20 mol%) and base (1.0 equiv) were allowed to react in DMF (2 mL). The reaction times and temperatures were evaluated, and good conversions to product 3a were reached under 70 o C for 24h for all reaction conditions.…”

“…A variety of solvents were evaluated (toluene, DMF, DMSO, MeCN, EtOH, and water), with best results employing polar aprotic solvents. We also could observe that use of iodide (KI) additive afforded better conversions of 3a, probably from in situ synthesis of more soluble K[BiI 4 ] catalyst. 5 The reaction scope is currently under investigation (scheme 1).…”

Synthesis of Seleno‐Heterocycles via Electrophilic/Radical Cyclization of Alkyne Containing Heteroatoms

“…NFSI plays a dual role as the oxidant and the amination reagent, the regio-and stereoselective chalcogenated enamides 334 were successfully synthesized (Scheme 106). [201][202] have focused on the use of Cu, [205][206][207] Fe, [208][209][210] Ag [211] and In-based [212] catalytic systems (Scheme 107). [203][204][205][206][207][208][209][210][211][212]…”

Transition-metal-free one-pot synthesis of alkynyl selenides from terminal alkynes under aerobic and sustainable conditions

“…Among them are reactions between lithium or sodium acetylides and electrophilic selenium reactants [23]. The use of hypervalent iodine(III) species [24] or alkynyl bromides with RSeLi [25] as nucleophilic selenium species or the reaction of alkynyl bromides under Cu catalysis [26–29], from terminal alkynes in the presence of bases and Cu [30–33], Fe [34–35] or In [36] catalysis, or with t- BuOK without of transition metal [37] have been reported. In general, these methodologies require selenyl halides or diselenides as starting materials, which limit their application.…”