24844-91-5Relevant academic research and scientific papers
Simple Nickel Salts for the Amination of (Hetero)aryl Bromides and Iodides with Lithium Bis(trimethylsilyl)amide
Martinez, Gabriel Espinosa,Nugent, Joseph W.,Fout, Alison R.
, p. 2941 - 2944 (2018)
Recent developments in the chemistry of C-N bond formation and the synthesis of anilines have allowed for the use of first-row transition metals to catalyze these transformations. Much of the progress in this area has been driven by comprehensive screening for privileged/tailored ligands, which can be costly and not readily available in a research laboratory setting. In this communication we report a protocol in which simple nickel salts catalyze the C-N cross-coupling reaction between (hetero)aryl bromides and iodides with lithium bis(trimethylsilyl)amide without the need for any additive ligand. This method is amenable to low nickel catalyst loadings (1%) as well as gram-scale reactions. Because of the good functional group tolerance and compatibility with heterocyclic moieties, this method is useful for academic laboratory settings where access to tailored ligands and noble-metal catalysts could be challenging.
Methyl transfer reaction from monomethyltin reagent under palladium(0) catalysis: A versatile method for labelling with carbon-11
Huiban, Mickael,Huet, Aline,Barre, Louisa,Sobrio, Franck,Fouquet, Eric,Perrio, Cecile
, p. 97 - 99 (2006)
The 11C-monomethylstannate prepared from [11C]-methyl iodide and Lappert's stannylene, was subject to a palladium-mediated cross-coupling reaction with an aryl halide under ligand-free conditions, to afford easily purified 11C-methyl(hetero)arenes in high radiochemical yields. The Royal Society of Chemistry 2006.
Deaminative Reductive Cross-Electrophile Couplings of Alkylpyridinium Salts and Aryl Bromides
Liao, Jennie,Basch, Corey H.,Hoerrner, Megan E.,Talley, Michael R.,Boscoe, Brian P.,Tucker, Joseph W.,Garnsey, Michelle R.,Watson, Mary P.
, p. 2941 - 2946 (2019/04/30)
A nickel-catalyzed reductive cross-coupling of alkylpyridinium salts and aryl bromides has been developed using Mn as the reductant. Both primary and secondary alkylpyridinium salts can be used, and high functional group and heterocycle tolerance is observed, including for protic groups. Mechanistic studies indicate the formation of an alkyl radical, and controlling its fate was key to the success of this reaction.
Synthesis of quinolines and fused pyridocoumarins from N-propargylanilines or propargylaminocoumarins by catalysis with gold nanoparticles supported on TiO2
Symeonidis, Theodoros S.,Lykakis, Ioannis N.,Litinas, Konstantinos E.
, p. 4612 - 4616 (2013/06/26)
[5,6]-Fused pyridocoumarins are prepared under mild conditions in excellent yields through the activation of the triple bond of 6-propargylaminocoumarins by gold nanoparticles supported on TiO2. The analogous reaction of N-propargylanilines with Au/TiO2 or Au/Al2O3 resulted in the formation of quinolines.
Homoleptic zincate-promoted room-temperature halogen-metal exchange of bromopyridines
Chau, Nguyet Trang Thanh,Meyer, Maxime,Komagawa, Shinsuke,Chevallier, Floris,Fort, Yves,Uchiyama, Masanobu,Mongin, Florence,Gros, Philippe C.
experimental part, p. 12425 - 12433 (2011/01/05)
Homoleptic lithium tri- and tetraalkyl zincates were reacted with a set of bromopyridines. Efficient and chemoselective bromine-metal exchanges were realized at room temperature with a substoichiometric amount of nBu 4ZnLi2·TMEDA reagent (1/3 equiv; TMEDA=N,N,N′,N′-tetramethylethylenediamine). This reactivity contrasted with that of tBu4ZnLi2·TMEDA, which was inefficient below one equivalent. DFT calculations allowed us to rationalize the formation of N...Li stabilized polypyridyl zincates in the reaction. The one-pot difunctionalization of dibromopyridines was also realized using the reagent stoichiometrically. The direct creation of C-Zn bonds in bromopyridines enabled us to perform efficient Negishi-type cross-couplings. Mild zincation! nBu4ZnLi2·TMEDA (in substoichiometric amounts) promoted efficient and chemoselective room-temperature bromine-metal exchange of a range of bromopyridines (see scheme). DFT calculations strongly supported the formation of a stabilized tripyridylzincate, which could be reacted with electrophiles or be directly involved in palladium-catalyzed cross-coupling reactions.
ACTIVATION OF REDUCING AGENTS. SODIUM HYDRIDE CONTAINING COMPLEX REDUCING AGENTS 23. SYMMETRICAL COUPLING OF NITROGEN-CONTAINING HETEROCYCLIC HALIDES
Vanderesse, R.,Lourak, M.,Fort, Y.,Caubere, P.
, p. 5483 - 5486 (2007/10/02)
The preparation of NiCRA (NaH-tBuONa-Ni(OAc)2) in the presence of PPh3 leads to a reagent (termed NiCRA-PPh3) which is shown to be one of the most efficient Ni containing reagents reported so far for the homocoupling of heteroaromatic halides.
Studies on Organometallic Compounds. III. Reaction of Trimethylstannylazines with Acyl Chlorides. A Novel C-C Bond Formation of Pyridine Nuclei
Yamamoto, Yutaka,Yanagi, Akihiko
, p. 2003 - 2010 (2007/10/02)
Introduction of an acyl group at the α-, β-, and γ-positions of pyridine nuclei was accomplished. 2-Trimethylstannyl-pyridine and -quinoline and 1-trimethylstannylisoquinoline directly reacted with various acyl chlorides to give the corresponding 2-pyridyl, 2-quinolyl, and 1-isoquinolyl ketones, respectively.Reaction of 3-trimethylstannylpyridine, -quinoline, and -isoquinoline with acyl chlorides proceeded smoothly under catalysis by PdCl2 or PdCl2(PPh3)2 to afford the corresponding ketones in good yields.Similary, 4-pyridyl, -quinolyl, and -isoquinolyl ketones were prepared from corresponding 4-trimethylstannyl derivatives and acyl chlorides.Keywords--trimethylstannylazine; palladium-catalyzed reaction; acylation; palladium dichloride; dichlorobis(triphenylphosphine)palladium(II)
