36856-92-5Relevant academic research and scientific papers
Alkali-metal mediated zincation of N-heterocyclic substrates using the lithium zincate complex, (THF)Li(TMP)Zn(tBu)2 and applications in in situ cross coupling reactions
Blair, Victoria L.,Blakemore, David C.,Hay, Duncan,Hevia, Eva,Pryde, David C.
supporting information; experimental part, p. 4590 - 4594 (2011/09/30)
This study investigates the ability of the mixed-metal reagent [Li(TMP)Zn(tBu)2] 1 to promote direct Zn-H exchange reactions (zincations) of a wide range of N-heterocyclic molecules. The generated metallated intermediates from these reactions are intercepted with I2 and some of them are also employed as precursors in Pd-catalysed Negishi cross-coupling applications. A comparison with recent precedents in metallation chemistry reveals that for some of these heterocycles, 1 allows improved conversions, under milder conditions and in certain cases, even gives unique regioselectivities.
An efficient and mild ortho-zincation of aromatics and heterocycles by using TMP2Mg·2LiCl in the presence of ZnCl2
Dong, Zhi-Bing,Zhu, Wei-Hua,Zhang, Zhi-Guang,Li, Min-Zhi
scheme or table, p. 775 - 780 (2010/04/25)
A variety range of functionalized aryl and heteroaryl zinc reagents were efficiently generated by using TMP2Mg·2LiCl (TMP = 2,2,6,6-tetramethylpiperamidyl) in the presence of ZnCl2. The subsequently functionalization gave after react
Direct zincation of functionalized aromatics and heterocycles by using a magnesium base in the presence of ZnCl2
Dong, Zhibing,Clososki, Giuliano C.,Wunderlich, Stefan H.,Unsinn, Andreas,Li, Jinshan,Knochel, Paul
experimental part, p. 457 - 468 (2009/06/24)
A wide range of polyfunctional aryl and heteroaryl zinc reagents were efficiently prepared in THF by using (TMP)2:Mg·2LiCl (TMP = 2,2,6,6-tetramethylpiperamidyl) in the presence of ZnCl2. The possible pathways of this metalation proc
Lithium-mediated zincation of pyrazine, pyridazine, pyrimidine, and quinoxaline
Seggio, Anne,Chevallier, Floris,Vaultier, Michel,Mongin, Florence
, p. 6602 - 6605 (2008/02/10)
(Chemical Equation Presented) Deprotonation of pyrazine, pyridazine, pyrimidine, and quinoxaline using an in situ mixture of ZnCl2· TMEDA (0.5 equiv) and LiTMP (1.5 equiv) was studied. Pyrazine and pyrimidine were deprotonated in THF at room te
Application of phosphonium salts to the reactions of various kinds of amides
Sugimoto, Osamu,Mori, Miho,Moriya, Keisuke,Tanji, Ken-Ichi
, p. 1112 - 1118 (2007/10/03)
The phosphonium salts 1 and 2 prepared from triphenylphosphine and N-halogenosuccinimide proved to be applicable to the conversion of amide compounds. Especially, halogenation of electron-deficient heteroaromatic alcohols with these reagents seems to be a convenient method compared to the halogenation with phosphorus oxyhalides.
