598-56-1Relevant articles and documents
Kaesz,Stone
, p. 6213,6214 (1960)
Deoxygenation of primary amides to amines with pinacolborane catalyzed by Ca[N(SiMe3)2]2(THF)2
Gong, Mingliang,Guo, Chenjun,Jiang, Linhong,Luo, Yunjie,Yu, Chong
supporting information, p. 1201 - 1206 (2021/05/29)
Deoxygenative reduction of amides is a challenging but favorable synthetic method of accessing amines. In the presence of a catalytic amount of Ca[N(SiMe3)2]2(THF)2, pinacolborane (HBpin) could efficiently reduce a broad scope of amides, primary amides in particular, into corresponding amines. Functional groups and heteroatoms showed good tolerance in this process of transformation, and a plausible reaction mechanism was proposed.
Reduction of Amides to Amines with Pinacolborane Catalyzed by Heterogeneous Lanthanum Catalyst La(CH2C6H4NMe2- o)3@SBA-15
Guo, Chenjun,Zhang, Fangcao,Yu, Chong,Luo, Yunjie
supporting information, p. 13122 - 13135 (2021/08/31)
Hydroboration of amides is a useful synthetic strategy to access the corresponding amines. In this contribution, it was found that the supported lanthanum benzyl material La(CH2C6H4NMe2-o)3@SBA-15 was highly active for the hydroboration of primary, secondary, and tertiary amides to amines with pinacolborane. These reactions selectively produced target amines and showed good tolerance for functional groups such as -NO2, -halogen, and -CN, as well as heteroatoms such as S and O. This reduction procedure exhibited the recyclable and reusable property of heterogeneous catalysts and was applicable to gram-scale synthesis. The reaction mechanisms were proposed based on some control experiments and the previous literature. This is the first example of hydroborative reduction of amides to amines mediated by heterogeneous catalysts.
Organic amine mediated cleavage of Caromatic-Cαbonds in lignin and its platform molecules
Cheng, Xiaomeng,Dong, Minghua,Han, Buxing,Liu, Huizhen,Liu, Shulin,Shen, Xiaojun,Wang, Zhenpeng,Xin, Yu,Yang, Junjuan
, p. 15110 - 15115 (2021/12/04)
The activation and cleavage of C-C bonds remains a critical scientific issue in many organic reactions and is an unmet challenge due to their intrinsic inertness and ubiquity. Meanwhile, it is crucial for the valorization of lignin into high-value chemicals. Here, we proposed a novel strategy to enhance the Caromatic-Cα bond cleavage by pre-functionalization with amine sources, in which an active amine intermediate is first formed through Markovnikov hydroamination to reduce the dissociation energy of the Caromatic-Cα bond which is then cleaved to form target chemicals. More importantly, this strategy provides a method to achieve the maximum utilization of the aromatic nucleus and side chains in lignin or its platform molecules. Phenols and N,N-dimethylethylamine compounds with high yields were produced from herbaceous lignin or the p-coumaric acid monomer in the presence of industrially available dimethylamine (DMA). This journal is
