123387-52-0Relevant articles and documents
Nano-ferrous ferric oxide (nano-Fe3O4): Powerful, reusable, and stable catalyst for N-Boc protection of amines
Zolfigol, Mohammad Ali,Moosavi-Zare, Ahmad Reza,Moosavi, Parvin,Khakyzadeh, Vahid,Zare, Abdolkarim
, p. 962 - 966 (2013)
Nano-ferrous ferric oxide (nano-Fe3O4) efficiently catalyzed N-boc protection of amines in high yields and acceptable reaction times. Nano-Fe3O4 was applied as an efficient, green, heterogeneous and reusable magnetite catalyst. Clean reaction, simple purification, short reaction time and high yield were some other advantages of this compound.
Synthesis, characterization and catalytic properties of monodispersed nano-sphere silica sulfuric acid
Zolfigol,Khazaei,Mokhlesi,Derakhshan-Panah
, p. 111 - 116 (2013)
In this research, the first report on synthesis of nano-sphere silica sulfuric acid (NS-SSA) as new catalyst was reported. The catalyst was prepared by the reaction of nano-sphere silica with chlorosulfonic acid at room temperature. The catalyst has been identified using various techniques (XRD, SEM, TEM, EDX, TGA, FT-IR) and results were shown that it was a spherical shape and its particle size was between 60 and 90 nm. The catalyst can be easily recovered and reused for seventeen reaction cycles for protection of amines without considerable loss of activity. It was found that the catalyst can be efficiently in large scale and we examined some reactions in scales of 50 and 100 mmol. Also, this method has some advantages such as high TOF of catalyst, chemoselectivity, easy work-up and short reaction time.
Sustainable Route Toward N-Boc Amines: AuCl3/CuI-Catalyzed N-tert-butyloxycarbonylation of Amines at Room Temperature
Cao, Yanwei,Huang, Yang,He, Lin
, (2021/12/22)
N-tert-butoxycarbonyl (N-Boc) amines are useful intermediates in synthetic/medicinal chemistry. Traditionally, they are prepared via an indirect phosgene route with poor atom economy. Herein, a step- and atom-economic synthesis of N-Boc amines from amines, t-butanol, and CO was reported at room temperature. Notably, this N-tert-butyloxycarbonylation procedure utilized ready-made substrates, commercially available AuCl3/CuI as catalysts, and O2 from air as the sole oxidant. This catalytic system provided unique selectivity for N-Boc amines in good yields. More significantly, gram-scale preparation of medicinally important N-Boc amine intermediates was successfully implement, which demonstrated a potential application prospect in industrial syntheses. Furthermore, this approach also showed good compatibility with tertiary and other useful alcohols. Investigations of the mechanisms revealed that gold catalyzed the reaction and copper acted as electron transfer mediator in the catalytic cycle.
Direct Hydrodecarboxylation of Aliphatic Carboxylic Acids: Metal- and Light-Free
Burns, David J.,Lee, Ai-Lan,McLean, Euan B.,Mooney, David T.
supporting information, p. 686 - 691 (2022/01/28)
A mild and inexpensive method for direct hydrodecarboxylation of aliphatic carboxylic acids has been developed. The reaction does not require metals, light, or catalysts, rendering the protocol operationally simple, easy to scale, and more sustainable. Crucially, no additional H atom source is required in most cases, while a broad substrate scope and functional group tolerance are observed.
A Fit-for-Purpose Synthesis of (R)-2-Methylazepane
Guizzetti, Sylvain,Michaut, Antoine,Federspiel, Guillaume,Eymard, Julien,Caron, Isabelle,Quatrevaux, Sabrina,Daras, Etienne,Jolly, Sandrine,Guillemont, Jér?me,Lan?ois, David
supporting information, p. 729 - 733 (2020/01/31)
The preparation of new RSV inhibitors required an efficient synthesis of (R)-2-methylazepane ((R)-1) amenable to large-scale production to support preclinical studies. After consideration of different options, an efficient five-step synthesis relying on t
Synthesis of Amide Enol Carbamates and Carbonates through Cu(OTf)2-Catalyzed Reactions of Ynamides with t-Butyl Carbamates/Carbonates
Han, Pan,Mao, Zhuo-Ya,Li, Ming,Si, Chang-Mei,Wei, Bang-Guo,Lin, Guo-Qiang
, p. 4740 - 4752 (2020/04/30)
A highly regioselective approach to access amide enol carbamates and carbonates 5a-5c′, 7a-7h, and 9 was developed through Cu(OTf)2-catalyzed reactions of ynamides 4 with t-butyl carbamates 2 and 8 and t-butyl carbonates 6. Moreover, this strategy was successfully applied to generate amide enol carbamates 11a-11s and 14a-14f from imides 10 and 13 with ynamides through an N-Boc cleavage-addition ring-opening process. A range of substituents was amenable to this transformation, and the desired amide enol carbamates and carbonates were obtained in moderate to good yields.
Direct α-Monofluoroalkenylation of Heteroatomic Alkanes via a Combination of Photoredox Catalysis and Hydrogen-Atom-Transfer Catalysis
Tian, Hao,Xia, Qing,Wang, Qiang,Dong, Jianyang,Liu, Yuxiu,Wang, Qingmin
supporting information, p. 4585 - 4589 (2019/06/17)
In this study, a new C(sp3)-H monofluoroalkenylation reaction involving cooperative visible-light photoredox catalysis and hydrogen-atom-transfer catalysis to afford products generated by selective hydrogen abstraction and radical-radical cross-coupling was described. This mild, efficient reaction shows high regioselectivity for the α-carbon atoms of amines, ethers, and thioethers and thus allows the preparation of monofluoroalkenes bearing various substituents. The reaction was applied to two bioactive molecules, indicating its utility for late-stage monofluoroalkenylation of compounds with inert C(sp3)-H bonds.
Photoredox-Mediated Direct Cross-Dehydrogenative Coupling of Heteroarenes and Amines
Dong, Jianyang,Xia, Qing,Lv, Xueli,Yan, Changcun,Song, Hongjian,Liu, Yuxiu,Wang, Qingmin
supporting information, p. 5661 - 5665 (2018/09/21)
A photoredox-mediated direct cross-dehydrogenative coupling reaction to accomplish α-aminoalkylation of N-heteroarenes is reported. This mild reaction has a broad substrate scope, offers the first general method for synthesis of aminoalkylated N-heteroarenes without the need for substrate prefunctionalization, and is scalable to the gram level. Furthermore, the reaction was found to be applicable to other hydrogen donors besides amines (i.e., ethers, an aldehyde, a formamide, p-xylene, and alkanes), thus enabling the preparation of N-heteroarenes bearing various types of substituents.
Preparation, characterization and application of succinimidinium hydrogensulfate ([H-Suc]HSO4) as an efficient ionic liquid catalyst for the N-Boc protection of amines
Shirini, Farhad,Jolodar, Omid Goli,Seddighi, Mohadeseh,Borujeni, Hojatollah Takbiri
, p. 19790 - 19798 (2015/03/18)
In this work, succinimidinium hydrogensulfate ([H-Suc]HSO4), as a novel Bronsted acidic ionic liquid is prepared and characterized by studying its FT-IR, 1H NMR, 13C NMR, mass and SEM. This reagent can be used as an efficient catalyst for the N-Boc protection of amines at room temperature and neat conditions. This new method consistently has the advantages of excellent yields and short reaction times. Further, this ionic liquid can be recovered and reused for several times. This journal is
{[[K.18-Crown-6]Br3}n: A tribromide catalyst for the catalytic protection of amines and alcohols
Chehardoli, Gholamabbas,Zolfigol, Mohammad Ali,Derakhshanpanah, Fateme
, p. 1730 - 1733 (2013/10/21)
{[K.18-Crown-6]Br3}n, a unique tribromide-type catalyst, was utilized for the N-boc protection of amines and trimethylsilylation (TMS) and tetrahydropyranylation (THP) of alcohols. The method is general for the preparation of N-boc derivatives of aliphatic (acyclic and cyclic) and aromatic, and primary and secondary amines and also various TMS-ethers and THP-ethers. The simple separation of the catalyst from the product is one of the many advantages of this method.
