79719-90-7Relevant academic research and scientific papers
Copper-Silver Dual Catalyzed Decyanative C–Se Cross-Coupling
Mukherjee, Nirmalya,Kundu, Debasish,Ranu, Brindaban C.
, p. 329 - 338 (2017)
Traditionally, a metal-catalyzed cross-coupling reaction is governed by displacement of leaving groups such as halogens, tosylates, etc. by different nucleophiles leading to the formation of carbon-carbon and carbon-heteroatom bonds. Besides displacement of traditional leaving groups in coupling reactions decyanative cross-coupling has also received current attention. The objective of this work is to develop a decyanative cross-coupling through metal-assisted nucleophilic displacement, which is less explored so far. Thus, a decyanative cross-coupling of aryl selenocyanate with aryl-/alkylacetylenes, boronic acids and silanes has been accomplished by a copper-assisted nucleophilic displacement reaction for an easy access to a series of diaryl, aryl alkyl, aryl vinyl and aryl alkynyl selenides. The best yield of product was obtained using 5 mol% of Cu(OAc)2, Ag2CO3(20 mol%) and Cs2CO3(1 equiv.) at 100 °C for 8 h in N-methylpyrrolidinone (NMP). The advantages of simple operation, high yields and general applicability make this procedure more attractive. A mechanistic pathway has been proposed. Silver plays a key role in the decyanation process. A plausible mechanistic pathway of this decyanative carbon-selenium cross-coupling has been proposed based on UV, EPR, HR-MS and IR analytical data along with results obtained from control experiments. (Figure presented.).
Silver-catalyzed carbon-selenium cross-coupling using N-(phenylseleno)phthalimide: An alternate approach to the synthesis of organoselenides
Mukherjee, Nirmalya,Pal, Subhajit,Saha, Amit,Ranu, Brindaban C.
, p. 51 - 56 (2017/01/10)
Silver(I) catalyzed phenylselenylation of terminal alkynes and organoboronic acids has been demonstrated using N-(phenylseleno)phthalimide as an electrophilic SePh donor. A wide variety of terminal alkynes and organoboronic acids are selenylated efficiently to produce the corresponding alkynyl and diaryl selenides, respectively, in good yields. Silver(I) acts as a Lewis acid in this process.
STEREOSELECTIVE SYNTHESIS OF VINYLIC SELENIDES
Comasseto, J. V.,Ferreira, J. T. B.,Petragnani, N.
, p. 287 - 294 (2007/10/02)
The addition of selenophenol to mono- and di-substituted unactivated acetylenes have been investigated.At room temperature the vinylic selenides obtained were predominantly of the Z configuration; at 120 deg C Z/E mixtures were produced.Vinylic selenides
