1150-51-2Relevant academic research and scientific papers
Iodine Promoted Conversion of Esters to Nitriles and Ketones under Metal-Free Conditions
Xiao, Jing,Guo, Fengzhe,Li, Yinfeng,Li, Fangshao,Li, Qiang,Tang, Zi-Long
, p. 2028 - 2035 (2021/02/03)
We report a novel strategy to prepare valuable nitriles and ketones through the conversion of esters under metal-free conditions. By using the I2/PCl3 system, various substrates including aliphatic and aromatic esters could react with acetonitrile and arenes to afford the desired products in good to excellent yields. This method is compatible with a number of functional groups and provides a simple and practical approach for the synthesis of nitrile compounds and aryl ketones.
Synthesis of Diverse Aromatic Ketones through C?F Cleavage of Trifluoromethyl Group
Ikeda, Mai,Matsuzawa, Tsubasa,Morita, Takamoto,Hosoya, Takamitsu,Yoshida, Suguru
supporting information, p. 12333 - 12337 (2020/09/09)
An efficient synthetic method of aromatic ketones through C?F cleavage of trifluoromethyl group is disclosed. The high functional group tolerance of the transformation and the remarkable stability of trifluoromethyl group in various reactions enabled mult
Sterically Hindered Ketones via Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling of Amides by N-C(O) Activation
Liu, Chengwei,Lalancette, Roger,Szostak, Roman,Szostak, Michal
, p. 7976 - 7981 (2019/10/10)
Herein, we report a new protocol for the synthesis of sterically hindered ketones that proceeds via palladium-catalyzed Suzuki-Miyaura cross-coupling of unconventional amide electrophiles by selective N-C(O) activation. Mechanistic studies demonstrate that steric bulk on the amide has a major impact, which is opposite to the traditional Suzuki-Miyaura cross-coupling of sterically hindered aryl halides. Structural and computational studies provide insight into ground-state distortion of sterically hindered amides and show that ortho-substitution alleviates the N-C(O) bond twist.
Catalytic Friedel-Crafts acylation: Magnetic nanopowder CuFe 2O4 as an efficient and magnetically separable catalyst
Parella, Ramarao,Naveen,Kumar, Amit,Babu, Srinivasarao Arulananda
, p. 1738 - 1742 (2013/03/28)
Catalytic regioselective Friedel-Crafts acylation of an array of anisoles/arenes with various acid chlorides using 5-20 mol % of magnetic nanopowder CuFe2O4 is reported. Unlike the conventional Friedel-Crafts reactions, which are catalyzed by moisture sensitive homogeneous catalysts/promoters, the nanopowder CuFe2O4 catalyst is moisture insensitive and the product/ketone-catalyst isolation is easily achieved using the magnetic properties of CuFe2O4.
Selective synthetic routes to sterically hindered unsymmetrical diaryl ketones via arylstannanes
Lo Fiego, Marcos J.,Silbestri, Gustavo F.,Chopa, Alicia B.,Lockhart, Maria T.
body text, p. 1707 - 1714 (2011/05/17)
Bulky arylstannanes and bulky aroyl chlorides are good reaction partners for the synthesis of two-, three-, and even four-ortho-substituted benzophenones, in good to excellent isolated yields (47-91%). Three simple and direct routes, with differential advantages, are proposed: (i) a catalyst-free protocol, in o-dichlorobenzene (ODCB) at 180 °C; (ii) a room temperature protocol, using AlCl3 (0.5 equiv), in dichloromethane (DCM); and (iii) a solvent-free, indium-promoted procedure. A radical mechanism is proposed for the indium-mediated reactions.2011 American Chemical Society.
Carboxylic Trifluoromethanesulfonic Anhydrides as Highly Effective Acylation Agents. - Perfluoroalkanesulfonic Acid Catalyzed Acylation of Arenes
Effenberger, Franz,Sohn, Erich,Epple, Gerhard
, p. 1195 - 1208 (2007/10/02)
Arene- and alkanecarboxylic trifluoromethanesulfonic anhydrides 2 and 5 are highly effective acylation agents, which react without Friedel-Crafts catalysts even with deactivated aromatics to yield aryl ketones 3 and 6, respectively.Acylation of arenes with carbonyl chlorides 4 and catalytic amounts of perfluoroalkanesulfonic acid gives ketones 3 and 6, resp., in good yields.Under similar conditions other strong Broensted acids show a considerably smaller degree of catalytic effect.
Acylierung von Aromaten mit Carbonsaeure-dihalogenphosphorsaeure-anhydriden
Effenberger, Franz,Koenig, Gerd,Klenk, Herbert
, p. 926 - 936 (2007/10/02)
Aryl ketones 4, 9 are formed in good yields without the addition of Friedel-Crafts catalysts from activated arenes (e. g. alkylbenzenes, anisole) and aryl- and alkylcarboxylic dihalophosphoric anhydrides 1, 2, and 7, 8, respectively.The anhydrides 7, 8 may be prepared in situ by mixing the respective carboxylic and dihalophosphoric anhydrides.This procedure is especially advantageous in care of the less stable compounds.
