5583-23-3Relevant academic research and scientific papers
Precious metal complexes of bis(pyridyl)allenes: Synthesis and catalytic and medicinal applications
Arnau Del Valle, Carla,Maliszewska, Hanna K.,Marín, María J.,Mu?oz, María Paz,Waller, Zo? A. E.,Xia, Ying
supporting information, p. 16739 - 16750 (2021/12/08)
The incorporation of donor-type substituents on the allene core opens up the possibility of coordination complexes in which the metal is bonded to the donor groups, with or without interaction with the double bond system. Despite the challenges in the syn
Transformation of Carbonyl Compounds into Homologous Alkynes under Neutral Conditions: Fragmentation of Tetrazoles Derived from Cyanophosphates
Yoneyama, Hiroki,Numata, Masahiro,Uemura, Kenji,Usami, Yoshihide,Harusawa, Shinya
, p. 5538 - 5556 (2017/06/07)
Cyanophosphates (CPs) can be easily prepared from either ketones or aldehydes, and their reaction with NaN3-Et3N·HCl results in the formation of azidotetrazoles. Under microwave irradiation, successive fragmentation of the azidotetrazoles generates alkylidene carbenes that undergo [1,2]-rearrangement and are transformed into homologous alkynes. Treatment of ketone-derived CPs with TMSN3 and Bu2SnO as catalyst in toluene at reflux directly yields the corresponding internal alkynes, whereas the reaction of aldehyde-derived CPs with NaN3-Et3N·HCl in THF at reflux or TMSN3-Bu2SnO (cat.) in toluene at reflux provides homologous terminal alkynes in good yields. These reactions take place under neutral conditions and can be successfully extended to obtain alkynes that are not usually accessible from the corresponding carbonyl compounds by the Ohira-Bestmann or Shioiri procedures, which require basic conditions.
Generation and reactions of pyridyllithiums via Br/li exchange reactions using continuous flow microreactor systems
Nagaki, Aiichiro,Yamada, Daisuke,Yamada, Shigeyuki,Doi, Masatomo,Ichinari, Daisuke,Tomida, Yutaka,Takabayashi, Naofumi,Yoshida, Jun-Ichi
, p. 199 - 207 (2013/03/28)
A continuous flow microreactor method for generating and carrying out reactions on pyridyllithiums has been developed based on Br/Li exchange reactions of bromopyridines and dibromopyridines. The reactions can be carried out without using cryogenic conditions by virtue of short residence times and efficient heat transfer, while very low temperatures such as-78 or-110°C are required for conventional batch macro methods. Moreover, sequential introduction of two different electrophiles has been successfully achieved using dibromopyridines in an integrated flow microreactor system composed of four micromixers and four microtube reactors.
Flow microreactor synthesis of disubstituted pyridines from dibromopyridines via Br/Li exchange without using cryogenic conditions
Nagaki, Aiichiro,Yamada, Shigeyuki,Doi, Masatomo,Tomida, Yutaka,Takabayashi, Naofumi,Yoshida, Jun-Ichi
supporting information; experimental part, p. 1110 - 1113 (2011/06/26)
A flow microreactor method for the synthesis of disubstituted pyridines by generation of pyridyllithiums followed by reactions with electrophiles has been developed. By using a short residence time and efficient temperature control, the cryogenic conditions required for conventional batch macro processes can be avoided. Sequential introduction of two different electrophiles into dibromopyridines has been achieved using an integrated flow microreactor system composed of four micromixers and four microtube reactors, to obtain disubstituted pyridine compounds.
