7476-71-3Relevant articles and documents
Zeolite catalyzed hydroarylation of alkenes with aromatic amines under organic ligand-free conditions
Li, Teng,Liu, Shujuan,Shi, Feng,Wang, Hongli,Wang, Xinzhi,Yuan, Hangkong,Zhao, Kang
, p. 18 - 29 (2021/01/12)
The hydroarylation of alkenes with aromatic amines is recognized as the most atom-economical and straightforward approach to obtain functional aromatic amines, which are versatile building blocks in organic synthesis and material chemistry. However, controllable synthesis of single hydroarylation product is still a significant challenge because hydroarylation reaction often delivers four hydroarylation products and hydroamination products are also produced during the reaction. Herein, we report the first example of heterogeneous zeolite catalyzed hydroarylation of styrene and norbornene with aniline derivatives under organic ligand-free conditions. With the USY zeolite as catalyst, a wide scope of alkenes and aromatic amines with various functional groups are smoothly converted into the corresponding products in 48–95% yields with high regioselectivity. Detailed characterizations revealed that Lewis acid can promote Hofmann-Martius rearrangement of hydroamination products toward hydroarylation products, resulting in high selectivity for hydroarylation products. In addition, it could be found that the weak acid sites of zeolite play a key role in forming hydroarylation products. Furthermore, the catalyst can be reused at least 10 times without obvious deactivation. This work may promote the development of heterogeneous catalyst system for alkene hydroarylation.
Synthesis of diarylmethanes via metal-free reductive cross-coupling of diarylborinic acids with tosyl hydrazones
Li, Xijing,Feng, Yuanyuan,Lin, Lin,Zou, Gang
, p. 10991 - 10995 (2013/02/22)
This paper describes a practical and efficient procedure that takes advantage of diarylborinic acids as a cost-effective alternative to arylboronic acids for synthesis of diarylmethanes through metal-free reductive cross-coupling with N-tosylhydrazones of aromatic aldehydes and ketones. The procedure tolerates hydroxyl, halide, amine, and allyl functionality, complementary to the transition-metal catalyzed cross-coupling techniques.
Dicationic electrophiles from olefinic amines in superacid
Zhang, Yun,McElrea, Aaron,Sanchez Jr., Gregorio V.,Do, Dat,Gomez, Alma,Aguirre, Sharon L.,Rendy, Rendy,Klumpp, Douglas A.
, p. 5119 - 5122 (2007/10/03)
This paper describes the superacid-catalyzed chemistry of olefinic amines and related compounds. A variety of olefinic amines are found to react with benzene in CF3SO3H (triflic acid) to give addition products in good yields (75-99%), including the pharmaceutical agents fenpiprane and prozapine. A general mechanism is proposed that invokes the formation of reactive, dicationic electrophiles and the direct observation of a diprotonated species is reported from low-temperature NMR experiments. This chemistry is also used to conveniently prepare functionalized polystyrene beads having pendant amine groups.