198012-02-1Relevant articles and documents
Palladium-Catalyzed Regioselective and Stereospecific Ring-Opening Suzuki-Miyaura Arylative Cross-Coupling of 2-Arylazetidines with Arylboronic Acids
Takeda, Youhei,Toyoda, Kazuya,Sameera,Tohnai, Norimitsu,Minakata, Satoshi
supporting information, p. 2796 - 2805 (2021/04/15)
We have developed a palladium-catalyzed regioselective and enantiospecific ring-opening Suzuki–Miyaura arylative cross-coupling of N-tosyl-2-arylazetidines to give enantioenriched 3,3-diarylpropylamines. This reaction represents an example of transition-metal-catalyzed ring-opening cross-coupling using azetidines as a non-classical alkyl electrophile. Density functional theory rationalized the mechanism of the full catalytic cycle, which consists of the selectivity-determining ring opening of the azetidine, reaction with water, rate-determining transmetalation, and reductive elimination. Transition states of the selectivity-determining ring-opening step were systematically determined by the multi-component artificial force induced reaction (MC-AFIR) method to explain the regioselectivity of the reaction. (Figure presented.).
One-Pot Synthesis of Diazirines and 15N2-Diazirines from Ketones, Aldehydes and Derivatives: Development and Mechanistic Insight
Ibert, Quentin,Cauwel, Madeleine,Glachet, Thomas,Tite, Tony,Le Nahenec-Martel, Patricia,Lohier, Jean-Fran?ois,Renard, Pierre-Yves,Franck, Xavier,Reboul, Vincent,Sabot, Cyrille
supporting information, p. 4390 - 4398 (2021/08/03)
Broad scope one-pot diazirine synthesis strategies have been developed using two different oxidants depending on the nature of the starting material. In all cases, an inexpensive commercial solution of ammonia (NH3) in methanol (MeOH) was emplo
Mild Darzens Annulations for the Assembly of Trifluoromethylthiolated (SCF3) Aziridine and Cyclopropane Structures
Delost, Michael D.,Njardarson, Jon T.
supporting information, p. 6121 - 6125 (2021/08/16)
We report mild new annulation approaches to trisubstituted trifluoromethylthiolated (SCF3) aziridines and cyclopropanes via Darzens inspired protocols. The products of these anionic annulations, rarely studied previously, possess attractive features rendering them valuable building blocks for synthesis platforms. In this study, trisubstituted acetophenone nucleophiles bearing SCF3 and bromine substituents in their α position were shown to undergo [2 + 1] annulations with vinyl ketones and tosyl-protected imines under mild reaction conditions.
Chiral-Directing-Group-Assisted Rhodium(III)-Catalyzed Asymmetric Addition of Inert Arene C?H Bond to Aldimines with Subsequent Intramolecular Cyclization
Cai, Xuhong,Chen, Wenkun,Nie, Ruifang,Wang, Jun
supporting information, p. 16611 - 16615 (2021/10/19)
By using a chiral directing group, an asymmetric rhodium(III)-catalyzed C?H bond addition to aldimines followed by intramolecular cyclization to form chiral isoindolinones has been achieved (up to 68 % yield, up to 93 % ee). A three-component variant that resembles Mannich reaction was also realized (41 % yield, 83 % ee). Product elaborations and preliminary mechanistic studies were described.
Copper-boryl mediated transfer hydrogenation of N-sulfonyl imines using methanol as the hydrogen donor
He, Yi,Li, Shi-Guang,Mbaezue, Ifenna I.,Reddy, Angula C.S.,Tsantrizos, Youla S.
supporting information, (2021/03/24)
B2Pin2-assisted copper-catalyzed transfer hydrogenation of aromatic sulfonylimines has been achieved, delivering a variety of aryl/heteroaryl sulfonamides in good to excellent yields under mild reaction conditions and with methanol a
Reductive alkylation of imines via asymmetric Cu-catalyzed addition of organozirconium reagents
Némethová, Ivana,Vargová, Denisa,Mudráková, Brigita,Filo, Juraj,?ebesta, Radovan
supporting information, (2020/01/08)
Chiral amines are important as medicines or agrochemicals. They are often assembled by nucleophilic addition to corresponding compounds featuring C[dbnd]N bond. Pre-made organometallics are typical nucleophiles in this reaction. In this work, we describe
The diastereoselective synthesis of 2,3-diaryl-3-cyano-substituted pyrrolidines via the MgI2 mediated ring expansion of aryl cyclopropyl nitriles
Stead, Darren
supporting information, (2020/09/04)
The MgI2 mediated reaction of aryl substituted cyclopropyl nitriles with tosyl aldimines to give 2,3-diaryl-3-cyano-substituted pyrrolidines has been demonstrated. In all cases, the trans-diastereoisomer was determined to be the major product.
Strategic vinyl sulfone nucleophile β-substitution significantly impacts selectivity in Vinylogous Darzens and aza-Darzens reactions
Delost, Michael D.,Njardarson, Jon T.
supporting information, p. 6917 - 6921 (2020/09/12)
Vinylogous Darzens and aza-Darzens reactions employing a benzothiophene 1,1-dioxide nucleophile are reported. These new [2 + 1] annulation reactions, which proceed under mild reaction conditions, are γ-selective, affording trans-epoxides selectively and favoring trans-aziridines. The reactions are base-dependent, with KOtBu and Cs2CO3 being optimal for aldehyde and imine annulations, respectively. Comparison of the benzothiophene nucleophile to its acyclic counterpart reveals superior performance in the case of aldehydes, while the outcome varies depending on the sulfonamide imine used.
Iron-based nanomaterials used as magnetic mesoporous nanocomposites to catalyze the preparation of N-sulfonylimines
Ashouri, Akram,Samadi, Saadi,Nasiri, Behzad,Bahrami, Zohre
, p. 549 - 556 (2019/08/01)
A new magnetic nanocatalyzed synthetic method for the synthesis of aldimines was evidenced. The reaction was carried out in a Schlenk tube under reflux conditions using various solvents and different nanomaterials as catalysts. In these reactions, an exce
NHC ligand-enabled Ni-catalyzed reductive coupling of alkynes and imines using isopropanol as a reductant
Yao, Wei-Wei,Li, Ran,Li, Jiang-Fei,Sun, Juan,Ye, Mengchun
supporting information, p. 2240 - 2244 (2019/05/17)
A nickel-catalyzed reductive coupling of alkynes and imines using readily available isopropanol as the reducing agent was developed. The use of a sterically bulky and electron-rich carbene ligand (AnIPr) significantly promotes the reaction, providing various multi-substituted allylic amines in 23-89% yield and the corresponding chiral ligand (AnIPr-3) can afford the products in 51-95% ee.