1036645-43-8Relevant academic research and scientific papers
Aryl bromides as inexpensive starting materials in the catalytic enantioselective arylation of aryl aldehydes: The additive TMEDA enhances the enantioselectivity
Yang, Yong-Xin,Liu, Yue,Zhang, Lei,Jia, Yan-E,Wang, Pei,Zhuo, Fang-Fang,An, Xian-Tao,Da, Chao-Shan
, p. 10696 - 10702 (2014)
We used aryl bromides as inexpensive starting materials to enantioselectively arylate aldehydes in one pot. Aryl bromides readily transfer aryls to aryllithiums with n-butyllithium, successively to triarylaluminums with aluminum chloride, and then to aryltitaniums with titanium isopropoxide. Finally aryltitaniums arylate aldehydes catalyzed by (S)-H8-BINOL-Ti(Oi-Pr)2 in excellent yields and enantioselectivities. The additive TMEDA evidently suppresses the racemic background reaction promoted by LiCl generated from salt metathesis. This procedure represents a cost-effective and operationally convenient method for enantioenriched diarylmethanols.
Bio-inspired asymmetric aldehyde arylations catalyzed by rhodium-cyclodextrin self-inclusion complexes
Asahi, Kaoru,Fujiwara, Shin-Ichi,Iwasaki, Takanori,Kambe, Nobuaki,Takahashi, Ryota,Tsuda, Susumu,Ueda, Ryoji,Yamauchi, Hiroki
supporting information, p. 801 - 807 (2022/02/03)
Transition-metal catalysts are powerful tools for carbon-carbon bond-forming reactions that are difficult to achieve using native enzymes. Enzymes that exhibit inherent selectivities and reactivities through host-guest interactions have inspired widesprea
Synthesis of planar chiral [2.2]Paracyclophanyl imidazo[1,5-a[pyridinium salts for the rhodium-catalyzed asymmetric arylation
Wang, Dengxia,Ma, Yudao,He, Fuyan,Duan, Wenzeng,Zhao, Lei,Song, Chun
, p. 810 - 825 (2013/02/25)
Several novel flexibility-restricted imidazo[1,5-a]pyridinium triflates (abbreviated as imidazolium salts) were synthesized from (4S p,13R p)-()-4-amino-13-bromo[2.2]paracyclophane and pyridylaldehyde. These imidazolium salts can be used as nitrogen-containing heterocyclic carbene precursors in asymmetric catalysis and here they are applied in the Rh-catalyzed asymmetric 1,2-addition of arylboronic acids to aldehydes. After optimizing the catalytic situations and testing a series of substrates, moderate enantioselectivity and good yield were obtained.
Synthesis of novel planar chiral Ag and Rh N-heterocyclic carbene complexes derived from [2.2]paracyclophane and their application in ultrasound assisted asymmetric addition reactions of organoboronic acids to aldehydes
Duan, Wenzeng,Ma, Yudao,He, Fuyan,Zhao, Lei,Chen, Jianqiang,Song, Chun
, p. 241 - 248 (2013/04/24)
Three novel planar chiral N-heterocyclic carbene silver and rhodium complexes based on [2.2]paracyclophane have been prepared. These could be used as catalysts/precatalysts for the asymmetric 1,2-addition of organoboronic acids to aldehydes. We optimized the reaction conditions and have applied ultrasonic irradiation in the asymmetric arylation for the first time. Under ultrasound irradiation, the combination of planar chiral NHC-Ag complex 5 and RhCl 3 can achieve higher catalytic activities in the asymmetric addition of organoboronic acids to aldehydes.
Synthesis of new alkoxy/sulfonate-substituted carbene precursors derived from [2.2]paracyclophane and their application in the asymmetric arylation of aldehydes
Duan, Wenzeng,Ma, Yudao,Qu, Bo,Zhao, Lei,Chen, Jianqiang,Song, Chun
, p. 1369 - 1375,7 (2012/12/12)
A series of novel planar chiral alkoxy/sulfonate-substituted carbene precursors have been designed and synthesized. They were used as N-heterocyclic carbene ligands in the Rh-catalyzed asymmetric addition of arylboronic acids to aromatic aldehydes, affording chiral diarylmethanols with high yields and moderate enantioselectivities.
Synthesis of new alkoxy/sulfonate-substituted carbene precursors derived from [2.2]paracyclophane and their application in the asymmetric arylation of aldehydes
Duan, Wenzeng,Ma, Yudao,Qu, Bo,Zhao, Lei,Chen, Jianqiang,Song, Chun
, p. 1369 - 1375 (2013/01/15)
A series of novel planar chiral alkoxy/sulfonate-substituted carbene precursors have been designed and synthesized. They were used as N-heterocyclic carbene ligands in the Rh-catalyzed asymmetric addition of arylboronic acids to aromatic aldehydes, affording chiral diarylmethanols with high yields and moderate enantioselectivities.
Planar chiral imidazolium salts based on [2.2]paracyclophane in the asymmetric rhodium-catalyzed 1,2-addition of arylboronic acids to aldehydes
Ma, Qingshuang,Ma, Yudao,Liu, Xiao,Duan, Wenzeng,Qu, Bo,Song, Chun
experimental part, p. 292 - 298 (2010/05/18)
A series of planar chiral imidazolium salts derived from [2.2]paracyclophane have been synthesized and characterized. By using these imidazolium salts as carbene precursors, the Rh-catalyzed 1,2-addition of arylboronic acids to aldehydes proceeded readily with low catalyst loadings (0.03-0.3 mol %) and gave a variety of chiral diarylmethanols in excellent yields and moderate enantioselectivities.
