- Reductive amination of ketones/aldehydes with amines using BH3N(C2H5)3as a reductant
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Herein, we report the first example of efficient reductive amination of ketones/aldehydes with amines using BH3N(C2H5)3 as a catalyst and a reductant under mild conditions, affording various tertiary and secondary amines in excellent yields. A mechanistic study indicates that BH3N(C2H5)3 plays a dual function role of promoting imine and iminium formation and serving as a reductant in reductive amination. This journal is
- Zou, Qizhuang,Liu, Fei,Zhao, Tianxiang,Hu, Xingbang
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supporting information
p. 8588 - 8591
(2021/09/04)
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- Transition-Metal-Free Three-Component Synthesis of Tertiary Aryl Amines from Nitro Compounds, Boronic Acids, and Trialkyl Phosphites
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The synthesis of aromatic amines is of continuous interest in chemistry. An exceptionally versatile three-component reaction that directly transforms inexpensive nitro compounds, boronic acids, and trialkyl phosphites into tertiary aromatic amines has been realized. The reaction tolerates alkyl and aryl substituents on the nitro and boronic acid moieties, as well as functionalized phosphites. No transition-metal catalysis is required. The method is orthogonal to other classical metal-catalyzed syntheses since it tolerates the presence of halogens, and also permits the synthesis of functionalized compounds such as α-amino ester derivatives. (Figure presented.).
- Roscales, Silvia,Csáky, Aurelio G.
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supporting information
p. 111 - 117
(2019/11/16)
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- Sodium Triethylborohydride-Catalyzed Controlled Reduction of Unactivated Amides to Secondary or Tertiary Amines
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The first transition-metal-free catalytic protocol for controlled reduction of amide functions using cheap and bench-stable hydrosilanes as reducing agents has been established. By altering the hydrosilane and solvent, the new method enables the selective cleavage of unactivated C-O bonds in amides and allows the C-N bonds to selectively break via the deacylated cleavage. Overall, this novel process may offer a versatile alternative to current methodologies employing stoichiometric metal systems for the controlled reduction of carboxamides.
- Yao, Wubing,He, Lili,Han, Deman,Zhong, Aiguo
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- Sodium Triethylborohydride-Catalyzed Controlled Reduction of Unactivated Amides to Secondary or Tertiary Amines
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The first transition-metal-free catalytic protocol for controlled reduction of amide functions using cheap and bench-stable hydrosilanes as reducing agents has been established. By altering the hydrosilane and solvent, the new method enables the selective cleavage of unactivated C-O bonds in amides and allows the C-N bonds to selectively break via the deacylated cleavage. Overall, this novel process may offer a versatile alternative to current methodologies employing stoichiometric metal systems for the controlled reduction of carboxamides.
- Yao, Wubing,He, Lili,Han, Deman,Zhong, Aiguo
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p. 14627 - 14635
(2019/12/02)
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- Method for selective reducing reaction of tertiary aryl amide and borane
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The present invention relates to a method for a selective reducing reaction of a tertiary aryl amide and borane. A tertiary amine product is prepared by the reducing reaction of a tertiary aryl amidederivative and a cheap and easily available organoboron reagent under mild conditions under the convenient catalysis of a non-transition metal compound sodium triethylborohydride used as a catalyst for the first time. Compared with traditional methods, the method of the method generally has the advantages of wide universality of a substrate, low cost and easy availability of the catalyst, and simplicity in reaction operation. The selective reducing reaction of the tertiary aryl amide compound and the organoboron reagent under the catalysis of the transition metal catalyst is realized for the first time, and a brand new "green" reaction strategy is provided for the laboratory preparation or industrial production of tertiary arylamine products.
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Paragraph 0057-0060
(2019/10/23)
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- Novel nonmetal catalytic bidirectional selective reduction method of tertiary aromatic amide
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The invention relates to a novel effective bidirectional selective environment-friendly method for hydrosilation reduction of tertiary aromatic amide and an organic silicon reagent. The method comprises the following steps: selecting a nonmetal catalytic system, and selectively preparing a secondary or tertiary organic amine compound by successively catalyzing tertiary aromatic amide and cheap PHMS or triethoxysilane under a mild condition. By adopting the method, the bidirectional selective reduction of the tertiary aromatic amide is realized by innovatively utilizing an electronic effect and steric hindrance difference of an organic silicon reagent at first time, so that a brand new strategy is provided for the reduction of amide and derivative of the amide, the defects of the traditional method that the substrate functional group is poor in compatibility, the production cost is high and the like can be overcome, and the application prospect of the amine compound prepared in industrial production or laboratory is promising.
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Paragraph 0066; 0067; 0068; 0069
(2017/10/22)
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- Borane-N,N-dialkylaniline hydroboration agents
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Borane-N,N-dialkylanilines represented by the formula wherein N is nitrogen, R is isobutyl or isopropyl and R' is straight or branched chain lower alkyl. The compounds are useful as hydroboration agents and for generating diborane.
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