- Copper-catalyzed oxidative benzylic C(sp3)-H amination: Direct synthesis of benzylic carbamates
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A new efficient strategy to access benzylic carbamates through C-H activation is reported. The use of a catalytic amount of a Cu(i)/diimine ligand in combination with NFSI ((PhSO2)2NF) or F-TEDA-PF6 as oxidants and H2NCO2R as an amine source directly leads to the C-N bond formation at the benzylic position. The mild reaction conditions and the broad substrate scope make this transformation a useful method for the late-stage incorporation of a ubiquitous carbamate fragment onto hydrocarbons. This journal is
- Liu, Shuai,Achou, Rapha?l,Boulanger, Coline,Pawar, Govind,Kumar, Nivesh,Lusseau, Jonathan,Robert, Frédéric,Landais, Yannick
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supporting information
p. 13013 - 13016
(2020/11/05)
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- Palladium-Catalyzed Amide Synthesis via Aminocarbonylation of Arylboronic Acids with Nitroarenes
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A palladium-catalyzed aminocarbonylation of aryl boronic acids with nitroarenes for the synthesis of amides has been developed. A wide range of substrates were well-tolerated and gave the corresponding amides in moderate to good yields. No external oxidant or reductant was needed in this procedure. This procedure provides a redox-economical process for the synthesis of amides.
- Peng, Jin-Bao,Li, Da,Geng, Hui-Qing,Wu, Xiao-Feng
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supporting information
p. 4878 - 4881
(2019/06/17)
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- Nickel/Briphos-Catalyzed Direct Transamidation of Unactivated Secondary Amides Using Trimethylsilyl Chloride
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Direct transamidation of secondary amides was developed via nickel catalysis. In the presence of trimethylsilyl chloride and manganese, Ni(diglyme)Cl2 with a Briphos ligand efficiently promoted the transamidation of N-aryl benzamide derivatives with primary amines to afford the corresponding secondary amides in moderate to good yields. Primary amines bearing electron-donating groups gave higher yields of the transamidation products.
- Yu, Subeen,Shin, Taeil,Zhang, Maosheng,Xia, Yuanzhi,Kim, Hyunwoo,Lee, Sunwoo
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supporting information
p. 7563 - 7566
(2019/01/03)
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- Ligand-free Pd(0)/SiO2-catalyzed aminocarbonylation of aryl iodides to amides under atmospheric CO pressure
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An efficient and facile route for CO-based carbonylation of aryl iodides with amines to synthesize amides has been established by using SiO2 supported Pd(0) as the catalyst in a mild basic environment (K2CO3). This ligand-free heterogeneous reaction model can afford amide products in good to excellent yields (up to 99%) under atmospheric CO pressure and moderate temperature. The supported catalyst also displayed a broad substrate scope, good functional group tolerance and good recyclability. These features render the as-provided carbonylation approach sustainable and applicable in organic synthesis.
- Hu, Qinhua,Wang, Lele,Wang, Chen,Wu, Yubin,Ding, Zhengxin,Yuan, Rusheng
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p. 37200 - 37207
(2017/08/09)
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- Synthesis of amides through an oxidative amidation of tetrazoles with aldehydes under transition-metal-free conditions
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A simple, inexpensive and efficient one-pot synthesis of amides was achieved in good yields via the direct oxidative amidation of tetrazoles with aldehydes under transition-metal-free conditions.
- Du, Juan,Luo, Kai,Zhang, Xiuli
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p. 54539 - 54546
(2015/01/09)
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- Synthesis of amides by palladium-catalyzed decarbonylative coupling of carboxylic acids with isocyanides
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Amides were synthesized from carboxylic acids and isocyanides under Pd II/AgI/base catalytic conditions. The reaction conditions were optimized, and the scope was studied. Various carboxylic acids and aryl isocyanides are compatible with this reaction, but alkyl isocyanides are not. A plausible mechanism, which features distinctive PdII-mediated decarbonylative coupling and unprecedented nucleophilic attack of carboxylates to PdII-ligated isocyanides, was proposed to account for this reaction. N-Arylamides are assembled in high yields from carboxylic acids and isocyanides under PdII/AgI/base catalytic conditions. The decarbonylative coupling features unprecedented nucleophilic attack of the carboxylate on the isocyanide, which acts as an electrophile as a result of its coordination to PdII, and this inverted reactivity is proposed to account for this transformation.
- Huang, Lin,Guo, Haili,Pan, Lingxia,Xie, Chunsong
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p. 6027 - 6031
(2013/09/24)
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- TiCl4 hiocarbonyls and oxidation of sulfides in the presence of H2O2
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H2O2 in combination with TiCl4 proved to be a highly reactive reagent system for the desulfurization of thioamide and thioketone derivatives in excellent yields and short reaction times with high purity. Sulfides were also found to undergo oxidation to sulfones under similar reaction conditions. In most cases, these reactions are highly selective, simple, and clean, affording products in high yields and purity.
- Bahrami, Kiumars,Khodaei, Mohammad M.,Shakibaian, Vida,Khaledian, Donya,Yousefi, Behrooz H.
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experimental part
p. 155 - 163
(2012/06/01)
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- H2O2/SOCl2: a useful reagent system for the conversion of thiocarbonyls to carbonyl compounds
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The H2O2/SOCl2 reagent system has been used as a new and efficient reagent for deprotection of thiocarbonyls to carbonyl compounds. The salient features of this protocol are short reaction times, good chemoselectivity, clean reaction profiles, and simple work-up that preclude the use of toxic solvents.
- Bahrami, Kiumars,Khodaei, Mohammad M.,Farrokhi, Azita
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supporting information; experimental part
p. 7658 - 7661
(2009/12/04)
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- Copper-catalyzed amidation of allylic and benzylic C-H bonds
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(Chemical Equation Presented) A copper-catalyzed amidation of allylic and benzylic C-H bonds with both primary and secondary sulfonamides is described. The reaction is applicable to the coupling of a diverse set of hydrocarbon species with aryl, heteroaryl, and alkyl sulfonamides and is tolerant of a variety of functional groups. Mechanistic insight has been gained through the isolation of a benzylic acetate intermediate, which was demonstrated to undergo facile conversion to the substituted sulfonamide product under copper catalysis.
- Pelletier, Guillaume,Powell, David A.
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p. 6031 - 6034
(2007/10/03)
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- Synthesis and QSAR studies in 2-(N-aryl-N-aroyl)amino-4,5-dihydrothiazole derivatives as potential antithrombotic agents
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A series of 2-(N-aryl-N-aroyl)amino-4,5-dihydrothiazole derivatives have been synthesized via cyclocondensation of N-aryl thioureas with 2-bromoethylamine hydrobromide followed by the reaction of the product thus obtained with aroyl chlorides. Title compounds were evaluated for their antithrombotic activity in vivo in mice where one of these compound 29 provided 65% protection as compared to 77% protection offered by the standard Indomethacin. Quantitative Structure-Activity Relationship (QSAR) studies were performed on these compounds using physicochemical (hydrophobic, electronic, steric) parameter as independent and antithrombic activity as dependent parameter, where antithrombotic activity correlated best (r > 0.8) with electronic parameters (F, σ or μ) having high statistical significance > 99.9% (F2,22 > 15.0; F2,22α:0.001 = 11.0) suggesting that hydrophobic, steric and resonance factors are insignificant in this set of molecules for the activity.
- Saxena, Anil K.,Pandey, Suresh K.,Seth,Singh,Dikshit,Carpy
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p. 2025 - 2034
(2007/10/03)
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