2388-50-3Relevant articles and documents
ALKYLATION OF THE SULFUR- AND NITROGEN-CONTAINING COMPOUNDS ANALOGOUS TO THIAZOLINE SYSTEMS.
Ohara,Akiba,Inamoto
, p. 1508 - 1513 (1983)
Work on alylation was extended to compounds containing both sulfur and nitrogen atoms analogous to thiazoline systems, in order to obtain information on the relation between the structure of the compound and the alkylated position. Possibility of intramolecular interaction between sulfonio and amino groups is discussed based on their NMR data.
Generation of Aryl and Heteroaryl Magnesium Reagents in Toluene by Br/Mg or Cl/Mg Exchange
Ziegler, Dorothée S.,Karaghiosoff, Konstantin,Knochel, Paul
supporting information, p. 6701 - 6704 (2018/05/05)
The alkylmagnesium alkoxide sBuMgOR?LiOR (R=2-ethylhexyl), which was prepared as a 1.5 m solution in toluene, undergoes very fast Br/Mg exchange with aryl and heteroaryl bromides, producing aryl and heteroaryl magnesium alkoxides (ArMgOR?LiOR) in toluene. These Grignard reagents react with a broad range of electrophiles, including aldehydes, ketones, allyl bromides, acyl chlorides, epoxides, and aziridines, in good yields. Remarkably, the related reagent sBu2Mg?2 LiOR (R=2-ethylhexyl) undergoes Cl/Mg exchange with various electron-rich aryl chlorides in toluene, producing diorganomagnesium species of type Ar2Mg?2 LiOR, which react well with aldehydes and allyl bromides.
Selective formylation and methylation of amines using carbon dioxide and hydrosilane catalyzed by alkali-Metal carbonates
Fang, Chi,Lu, Chunlei,Liu, Muhua,Zhu, Yiling,Fu, Yao,Lin, Bo-Lin
, p. 7876 - 7881 (2018/05/23)
The formylation and methylation of amines with carbon dioxide and hydrosilanes are emerging yet important types of transformations for CO2. Catalytic methods effective for both reactions with wide substrate scopes are rare because of the difficulty in controlling the selectivity. Herein, we report that simple and readily available inorganic bases alkali-metal carbonates, especially cesium carbonatecatalyze both the formylation and methylation reactions efficiently under mild conditions. The selectivity can be conveniently controlled by varying the reaction temperature and silane. A “cesium effect” on both reactions was observed by comparing the catalytic activity of various alkali-metal carbonates. Combined experimental and computational studies suggested the following reaction mechanism: (i) activation of Si?H by Cs2CO3, (ii) insertion of CO2 into Si?H, (iii) formylation of amines by silyl formate, and (iv) reduction of formamides to methylamines.
N-heterocyclic carbene copper(i) catalysed N-methylation of amines using CO2
Santoro, Orlando,Lazreg, Fama,Minenkov, Yury,Cavallo, Luigi,Cazin, Catherine S. J.
, p. 18138 - 18144 (2015/10/28)
The N-methylation of amines using CO2 and PhSiH3 as source of CH3 was efficiently performed using a N-heterocyclic carbene copper(i) complex. The methodology was found compatible with aromatic and aliphatic primary and secondary amines. Synthetic and computational studies have been carried out to support the proposed reaction mechanism for this transformation.
