- Tin-Catalyzed Selective Reductive Hydroamination of Alkynes for the Synthesis of Tertiary Amines
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A unique preference of tin(II) for aniline activation is disclosed. In the present work tin(II) triflate-catalyzed highly selective Markovnikov reductive hydroamination of internal as well as terminal alkynes is reported. The mechanistic study revealed the involvement of two steps in one pot wherein alkyne reduces to corresponding alkene in presence of PMHS as reducing agent followed by hydroamination of alkene. A broad range of alkynes transformed into tertiary amines with good to excellent yield. This method is equally applicable in synthesis of secondary amines.
- Nayal, Onkar S.,Thakur, Maheshwar S.,Kumar, Manoranjan,Sharma, Sushila,Kumar, Neeraj
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p. 1103 - 1109
(2016/04/19)
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- Titania nanoparticles stabilized HPA in SBA-15 for the intermolecular hydroamination of activated olefins
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A liquid phase hydroamination (HA) of α,β-ethylenic compounds with amines was investigated with TiO2 nanoparticles stabilized 12-tungstophosphoric acid (TPA) in SBA-15. The catalysts were prepared by wet impregnation of TPA/TiO2 nanoparticles into the SBA-15 and calcined at different temperatures. The characterization results reveal that the textural properties and the acidity of the prepared catalysts can be finely controlled with the simple adjustment of the calcination temperature and the structure of the support, decorated with the TiO2 and TPA nanoparticles, was intact even after the modification. The prepared catalysts were investigated for HA of ethyl acrylate with different aromatic and aliphatic amines over a wide range of reaction conditions to optimize the yield and the selectivity of product. It was found that this process is 100% atom efficient and the catalytic performance depended significantly on the loading of TPA over the catalyst and the calcination temperature. Under optimized reaction conditions, the best catalyst, 15 wt%TPA/22.4 wt%TiO2/SBA-15 calcined at 1123 K, offered the highest conversion of p-ethylaniline (70%) with 100% chemo-selectivity to the anti-Markovnikov product, i.e., the mono-addition product. The reaction was heterogeneously catalyzed and no contribution from leached TPA into the reaction was observed.
- Sawant-Dhuri, Dhanashri,Balasubramanian, Veerappan V.,Ariga, Katsuhiko,Park, Dae-Hwan,Choy, Jin-Ho,Cha, Wang Soo,Al-Deyab, Salem S.,Halligudi, Shivappa B.,Vinu, Ajayan
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p. 3347 - 3354
(2015/04/16)
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- SYNERGISTS
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Compounds of formula (I): wherein Ar represents an, optionally substituted, aryl or heteroaryl group, R represents an, optionally substituted, aryl or heteroaryl group, an optionally substituted straight or branched chain C1.10-alkyl, R1/
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Page/Page column 24
(2011/10/13)
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- Cerium(IV) ammonium nitrate (CAN) catalyzed aza-Michael addition of amines to α,β-unsaturated electrophiles
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Cerium(IV) ammonium nitrate (CAN) catalyzed facile and efficient aza-Michael addition of aromatic and aliphatic amines with α,β-unsaturated electrophiles in the absence of solvent under ultrasound irradiation.
- Duan, Zheng,Xuan, Xuejie,Li, Ting,Yang, Chenfei,Wu, Yangjie
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p. 5433 - 5436
(2007/10/03)
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- The preparation of functionalized amines and amides using benzotriazole derivatives and organozinc reagents
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Secondary and tertiary amines 6 are conveniently prepared in good yields by reacting organozinc halides with adducts 4, which are derived from the corresponding amines, aldehydes and benzotriazole. The use of organozinc reagents enables the introduction of nitro, cyano or ester functionalities into amine mainframes. This methodology was also used to prepare functionalized amides 8.
- Katritzky, Alan R.,Strah, Sonja,Belyakov, Sergei A.
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p. 7167 - 7178
(2007/10/03)
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