70414-49-2Relevant academic research and scientific papers
Tandem Photoredox Catalysis: Enabling Carbonylative Amidation of Aryl and Alkylhalides
Connell, Timothy U.,Forni, José A.,Micic, Nenad,Polyzos, Anastasios,Weragoda, Geethika
supporting information, p. 18646 - 18654 (2020/08/21)
We report a new visible-light-mediated carbonylative amidation of aryl, heteroaryl, and alkyl halides. A tandem catalytic cycle of [Ir(ppy)2(dtb-bpy)]+ generates a potent iridium photoreductant through a second catalytic cycle in the presence of DIPEA, which productively engages aryl bromides, iodides, and even chlorides as well as primary, secondary, and tertiary alkyl iodides. The versatile in situ generated catalyst is compatible with aliphatic and aromatic amines, shows high functional-group tolerance, and enables the late-stage amidation of complex natural products.
Thioamide-Directed Cobalt(III)-Catalyzed Selective Amidation of C(sp3)?H Bonds
Tan, Peng Wen,Mak, Adrian M.,Sullivan, Michael B.,Dixon, Darren J.,Seayad, Jayasree
supporting information, p. 16550 - 16554 (2017/12/07)
A mild, oxidant-free, and selective Cp*CoIII-catalyzed amidation of thioamides with robust dioxazolone amidating agents via C(sp3)?H bond activation to generate the desired amidated products is reported. The method is efficient and allows for the C?H amidation of a wide range of functionalized thioamides with aryl-, heteroaryl-, and alkyl-substituted dioxazolones under the Cp*CoIII-catalyzed conditions. The observed regioselectivity towards primary C(sp3)?H activation is supported by computational studies and the cyclometalation is proposed to proceed by means of an external carboxylate-assisted concerted metalation/deprotonation mechanism. The reported method is a rare example of the use of a directing group other than the commonly used pyridine and quinolone classes for Cp*CoIII-catalyzed C(sp3)?H functionalization and the first to exploit thioamides.
Rhodium-Catalyzed oxidative amidation of sterically hindered aldehydes and alcohols
Nguyen, Trang T.,Hull, Kami L.
, p. 8214 - 8218 (2018/05/23)
A rhodium-catalyzed oxidative amidation reaction has been developed with sterically hindered aldehydes and alcohols for the synthesis of amides containing a quaternary carbon at the α position. A variety of amine nucleophiles, both aliphatic and aromatic, are employed and afford the corresponding amides in good to excellent yields. Finally, mechanistic studies are performed to gain insight into both catalytic cycles.
Amide formation using in situ activation of carboxylic acids with [Et 2NSF2]BF4
Mahe, Olivier,Desroches, Justine,Paquin, Jean-Francois
, p. 4325 - 4331 (2013/07/26)
The formation of amides through the in situ activation of carboxylic acids with [Et2NSF2]BF4 is presented. A wide range of carboxylic acids and amines were used to produce the corresponding amides in up to 99 % yield. The reaction of hindered amines was also possible in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) under slightly modified conditions. An enantiopure carboxylic acid and amine were both shown to react without racemization. Copyright
Samarium-mediated mild and facile method for the synthesis of amides
Shi, Feng,Li, Jian,Li, Chunju,Jia, Xueshun
experimental part, p. 6049 - 6051 (2010/11/21)
Samarium-mediated facile method for the formation of amide bonds by the reaction of acyl chlorides and amines is described. The reaction afforded high yields of the desired amides under mild and neutral conditions.
Stereoselective syntheses of trisubstituted olefins via platinum catalysis: α-Silylenones with geometrical complementarity
Rooke, Douglas A.,Ferreira, Eric M.
supporting information; experimental part, p. 11926 - 11928 (2010/11/16)
The stereoselective syntheses of α-silylenones using catalytic PtCl2 are reported. Via alkyne activation, α- hydroxypropargylsilanes are converted to (Z)-silylenones through a highly selective silicon migration. The complementary (E)-silylenone
Thio FCMA intermediates as strong acyl donors: A general solution to the formation of complex amide bonds
Rao, Yu,Li, Xuechen,Danishefsky, Samuel J.
supporting information; experimental part, p. 12924 - 12926 (2009/12/07)
(Chemical Equation Presented) Novel methodology for the formation of amide bonds under neutral conditions is described. Evidence is presented that the active acyl donors are thio FCMA intermediates, generated from the reactions of thioacids with isonitril
Leishmanicidal potential of N-substituted morpholine derivatives: Synthesis and structure-activity relationships
Khan, Khalid Mohammed,Khan, Muhammad Zarrar,Taha, Muhammad,Maharvi, Ghulam Murtaza,Saify, Zafar Saeed,Parveen, Shahnaz,Choudhary, Muhammad Iqbal
experimental part, p. 479 - 484 (2010/06/21)
A series of N-substituted morpholines 2-20 was synthesised by reacting various acid chlorides and alkyl halides with morpholine (1). All of the synthesised compounds 2-20 were screened for their leishmanicidal effects using amphotericin B (IC50 = 0.24 μg L-1) and pentamidine (IC50 = 2.56 μg mL-1) as standards and a structure-activity relationship (SAR) study was established. The compounds 2 (IC50 = 48 μg mL-1), 3 (IC50 = 30.0 μg mL-1), 10 (IC50 = 41.0 μg mL-1), 15 (IC50 = 33.0 μg mL-1), 16 (IC50 = 35.0 μg mL-1) and 20 (IC50 = 47.0 μg mL-1) showed weak leishmanicidal activities.
Preparation of tertiary amides from carbamoyl chlorides and organocuprates
Lemoucheux, Laurent,Seitz, Thomas,Rouden, Jacques,Lasne, Marie-Claire
, p. 3703 - 3706 (2007/10/03)
(Chemical Equation Presented) Reaction of carbamoyl chlorides with cyano-Gilman cuprates affords tertiary amides in good to excellent yields. The reaction is general due to the possibility of using reagents made either from organolithium or from Grignard compounds. The characterization of the main side products allowed for the suggestion of a possible mechanism.
BIFUNCTIONAL CATALYSTS
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Page 43, (2010/02/10)
Bifunctional Lewis acid - Lewis base catalyst of Formula (I): wherein O is a C2-60 optionally heteroatom containing substituted or unsubstituted hydrocarbon scaffold comprising pendant or integral bifunctional groups LA and LB wherein LA is a pendant or integral boron or silicon Lewis acid group and LB is a pendant or integral phosphorus or nitrogen Lewis base group and its salts, N-fanctionalised derivatives, dimer or oligomer thereof; processes for the preparation thereof; novel compounds and novel intermediates; a composition comprising a catalyst or compound of the invention; a kit comprising one or more catalysts; the use thereof as catalysts in selective transformations, kits therefor and processes for selective transformation reactions catalysed thereby; screening methods to identify catalysts for specific transformations; and kits therefor.
