356554-06-8Relevant articles and documents
Enantioselective addition of thiophenylboronic acids to aldehydes using ZnEt2/Schiff-base catalytic system
Liu, Xiaodong,Qiu, Li,Hong, Liang,Yan, Wenjing,Wang, Rui
, p. 616 - 620 (2009)
Using Schiff-base amino alcohols as catalysts which were readily derived from natural amino acids in three steps, a series of valuable optically active thiophenyl methanols (4a-4n) were first obtained in good yields and high enantioselectivities (up to 96% ee) through the asymmetric addition of thiophenylboronic acid to aldehydes in the presence of ZnEt2 in toluene. Crown Copyright
Asymmetric Transfer Hydrogenation of Aryl Heteroaryl Ketones using Noyori-Ikariya Catalysts
Zheng, Ye,Martinez-Acosta, Jaime A.,Khimji, Mohammed,Barbosa, Luiz C. A.,Clarkson, Guy J.,Wills, Martin
, p. 4384 - 4391 (2021/08/23)
A range of ketones flanked by a combination of an aromatic and a heterocyclic ring (furan, thiophene, N-methylimidazole) were reduced under asymmetric transfer hydrogenation (ATH) conditions. Using a range of [(arene)Ru(TsDPEN)Cl] precatalysts, including tethered derivatives, the reduction enantioselectivity was high (up to 99 % ee) in cases where the aromatic ring contained an ortho-substituent. The enantioselectivity is influenced by a combination of steric and electronic factors which for the furan and thiophene series, follow literature precedents. In the case of the N-methylimidazole-containing ketones, an unexpected switch in enantioselectivity took place upon variation of the opposing aromatic group. Pyrrole- containing ketones were resistant to reduction. This study demonstrates the asymmetric transfer hydrogenation (ATH) of a range of hindered heterocyclic ketones, in high conversion and ee, using Noyori-Ikariya catalysts.
CoI-Catalyzed Barbier Reactions of Aromatic Halides with Aromatic Aldehydes and Imines
Presset, Marc,Paul, Jér?me,Cherif, Ghania Nait,Ratnam, Nisanthan,Laloi, Nicolas,Léonel, Eric,Gosmini, Corinne,Le Gall, Erwan
supporting information, p. 4491 - 4495 (2019/02/27)
The reductive Barbier coupling of aromatic halides and electrophiles has been achieved using a CoBr2/1,10-phenanthroline catalytic system and over stoichiometric amounts of zinc. The reaction displayed a broad scope of substrates, including (hetero)aryl chlorides as pro-nucleophiles and aldehydes or imines as electrophiles, leading to diarylmethanols and diarylmethylamines in moderate to excellent yields, respectively.
Thiophene containing trisubstituted methanes [TRSMs] as identified lead against Mycobacterium tuberculosis
Singh, Priyanka,Manna, Sudipta Kumar,Jana, Amit Kumar,Saha, Tiash,Mishra, Pankaj,Bera, Saurav,Parai, Maloy Kumar,Srinivas Lavanya Kumar,Mondal, Sankalan,Trivedi, Priyanka,Chaturvedi, Vinita,Singh, Shyam,Sinha, Sudhir,Panda, Gautam
, p. 357 - 368 (2015/04/14)
Triarylmethanes (TRAMs) and thiophene containing trisubstituted methanes (TRSMs) have been reported by us, having potential against Mycobacterium tuberculosis and Mycobacterium fortuitum strains, respectively. Further, extension through synthesis and biol
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.
