137521-24-5Relevant articles and documents
Oxidative decarboxylation of α-amino acids: A mild and efficient method for the generation of N-acyliminium ions
Boto, Alicia,Hernandez, Rosendo,Suarez, Ernesto
, p. 5945 - 5948 (1999)
The oxidative decarboxylation of α-amino acids using the system (diacetoxyiodo)benzene or iodosylbenzene and iodine proceeded smoothly at room temperature. The intermediacy of an N-acyliminium cation has been demonstrated through intermolecular and intram
Kato et al.
, (1962)
Micellar Catalysis for Sustainable Hydroformylation
Calamante, Massimo,Dei, Filippo,Maramai, Samuele,Migliorini, Francesca,Petricci, Elena
, p. 2794 - 2806 (2021/05/03)
It is here reported a fully sustainable and generally applicable protocol for the regioselective hydroformylation of terminal alkenes, using cheap commercially available catalysts and ligands, in mild reaction conditions (70 °C, 9 bar, 40 min). The process can take advantages from both micellar catalysis and microwave irradiation to obtain the linear aldehydes as the major or sole regioisomers in good to high yields. The substrate scope is largely explored as well as the application of hydroformylation in tandem with intramolecular hemiacetalization thus demonstrating the compatibility with a broad variety of functional groups. The reaction is efficient even in large scale and the catalyst and micellar water phase can be reused at least 5 times without any impact in reaction yields. The efficiency and sustainability of this protocol is strictly related to the in situ transformation of the aldehyde into the corresponding Bertagnini's salt that precipitates in the reaction mixture avoiding organic solvent mediated purification steps to obtain the final aldehydes as pure compounds.
Easily accessible and highly tunable bisphosphine ligands for asymmetric hydroformylation of terminal and internal alkenes
Xu, Kun,Zheng, Xin,Wang, Zhiyong,Zhang, Xumu
, p. 4357 - 4362 (2014/05/06)
An efficient methodology for synthesizing a small library of easily tunable and sterically bulky ligands for asymmetric hydroformylation (AHF) has been reported. Five groups of alkene substrates have been tested with excellent conversions, moderate-to-excellent regio- and enantioselectivities. Among the best result of the reported literature, application of ligand 1 c in the highly selective AHF of the challenging substrate 2,5-dihydrofuran yielded almost one isomer in up to 99 % conversion along with enantiomeric excesses (ee) of up to 92 %. Highly enantioselective AHF of dihydropyrrole substrates is achieved using the same ligand, with up to 95 % ee and up to >1:50 β-isomer/α- isomer ratio. The simpler the better! An efficient method for the easy and tunable synthesis of a series of asymmetric hydroformylation (AHF) ligands from low-cost, commercially available starting materials has been reported. These ligands can give excellent conversions and moderate to excellent regio- and enantioselectivities for a broad range of mono- and disubstituted alkenes with a low catalyst loading (substrate-to-catalyst ratios (S/C) of 1000:1 to 3000:1).
