68395-76-6Relevant academic research and scientific papers
Selective Difunctionalization of Unactivated Aliphatic Alkenes Enabled by a Metal-Metallaaromatic Catalytic System
Cui, Fei-Hu,Fei, Jiawei,Gao, Le-Han,Hua, Yuhui,Lin, Yu-Mei,Xia, Haiping,Zhao, Xiaodan
supporting information, (2022/02/10)
The design of organometallic catalysts is crucial in the development of catalytic reactions. Herein, we describe a heterometallic [Os-Cu] complex with the characteristics of bimetallics, metallaaromatics, and pincer complexes. This complex serves as a highly effective catalyst for selective amino- and oxyselenation of unactivated alkenes. More than 80 examples including challenging substrates of unsymmetric aliphatic alkenes and amine-based nucleophiles in such reactions are provided. These reactions produce 1,2-difunctionalized products with good yields and high levels of chemo-, regio-, and stereoselectivity. Our studies revealed the following: (i) The usually inert osmium center activates the N- or O-centered nucleophiles. (ii) The copper-osmium bonding and its cooperative effects play essential roles in control the selectivity by bringing the reaction components into close proximity. (iii) The metallaaromatic moiety helps to stabilize the intermediate. These findings provide a versatile platform for catalyst design based on metal-metallaaromatic cooperative effects that have not been attained previously with bimetallic complexes.
Visible light photocatalyzed direct conversion of aryl-/heteroarylamines to selenides at room temperature
Kundu, Debasish,Ahammed, Sabir,Ranu, Brindaban C.
, p. 1814 - 1817 (2014/04/17)
A novel strategy for the direct conversion of aryl- and heteroarylamines to selenides has been developed via diazotization of amines with tert-butyl nitrite in neutral medium followed by reaction with diaryl/diheteroaryl/dialkyl diselenides in one pot under photocatalysis at room temperature in the absence of any metal. This reaction is also applied for the synthesis of tellurides. The selenylation of heteroarylamine by this protocol is of much significance because of the difficulty in diazotization of these molecules by a standard diazotization method in acid medium.
Synthesis of arylseleno-1,2,3-triazoles via copper-catalyzed 1,3-dipolar cycloaddition of azido arylselenides with alkynes
Deobald, Anna M.,Camargo, Leandro R.S.,Hoerner, Manfredo,Rodrigues, Oscar E.D.,Alves, Diego,Braga, Antonio L.
scheme or table, p. 2397 - 2406 (2011/09/15)
The use of organoselenium compounds in the copper-catalyzed Huisgen 1,3-dipolar cycloaddition of azido arylselenides with various alkynes is described. Arylseleno-1,2,3-triazoles are prepared in excellent yields via reaction of amino arylselenides with is
An efficient copper(I) iodide catalyzed synthesis of diaryl selenides through Cse bond formation using solvent acetonitrile as ligand
Dandapat, Arpan,Korupalli, Chiranjeevi,Prasad,Singh, Rahul,Sekar, Govindasamy
experimental part, p. 2297 - 2302 (2011/09/16)
A wide range of diaryl selenides can be synthesized through CSe bond formation using readily available copper(I) iodide as catalyst under mild reaction conditions (82C) from aryl iodides and diphenyl diselenide. In this coupling reaction, solvent acetonitrile acts as ligand for copper(I) iodide and no external ligand is required. Less reactive aryl bromides also provide the di-aryl selenides in good isolated yields. Georg Thieme Verlag Stuttgart ? New York.
Synthesis of azido arylselenides and azido aryldiselenides: a new class of selenium-nitrogen compounds
Deobald, Anna Maria,Simon de Camargo, Leandro R.,Tabarelli, Greice,H?rner, Manfredo,Rodrigues, Oscar E.D.,Alves, Diego,Braga, Ant?nio L.
experimental part, p. 3364 - 3367 (2010/08/19)
We present here our results of the efficient synthesis of azido arylselenides and azido aryldiselenides under mild conditions. Starting from nitrogen-substituted benzenes, we incorporated selenium atom at aromatic ring and obtained amino arylselenides and diselenides in satisfactory yields. Treatment of these compounds with iso-pentyl nitrite (i-C5H11ONO) and azido trimethylsilane (Me3SiN3) in THF affords a variety of azido arylselenides and diselenides in good to excellent yields.
Methods for formation of aryl-sulfur and aryl-selenium compounds using copper(I) catalysts
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Page/Page column 15-16; 41, (2008/06/13)
A mild, palladium-free synthetic protocol for the cross-coupling reaction of vinyl or aryl iodides and thiols or selenols using, in certain embodiments, 10 mol % CuI and 10 mol % neocuproine, with NaOt-Bu as the base, in toluene at 110 ° C. A variety of vinyl/aryl sulfides and vinyl/aryl selenides can be synthesized in excellent yields from readily available iodides and thiols or selenols.
A general method for the formation of diaryl selenides using copper(I) catalysts
Gujadhur, Rattan K.,Venkataraman
, p. 81 - 84 (2007/10/03)
We report a mild, palladium-free synthetic protocol for the cross coupling reaction of aryl iodides and phenyl selenol using 10 mol% CuI/neocuproine, NaOt-Bu or K2CO3 as base, in toluene, at 110°C. Using this protocol, we show that a variety of diaryl selenides can be synthesized in good yields from commercially available aryl iodides.
