536-80-1Relevant articles and documents
Lucas,Kennedy,Formo
, p. 483 (1955)
Chiral-at-Ruthenium Catalyst with Sterically Demanding Furo[3,2-b]pyridine Ligands
Cui, Tianjiao,Qin, Jie,Harms, Klaus,Meggers, Eric
, p. 195 - 198 (2019)
A sterically demanding derivative of a previously introduced chiral-at-metal ruthenium(II) catalyst scaffold is introduced. It is composed of two bidentate furo[3,2-b]pyridyl functionalized N-heterocyclic carbene ligands. Their cis-coordination generates helical chirality and a stereogenic ruthenium center. Two additional labile acetonitriles compose the catalytic site which is highly shielded by two 2-(tert-butyl)furo[3,2-b]pyridine moieties. The synthesis of the non-racemic ruthenium catalyst and its catalytic properties for the enantioselective alkynylation of 2,2,2-trifluoroacetophenone and pentafluorobenzaldehyde are reported and compared with sterically less demanding derivatives.
Modifying the Product Distribution of a Reaction within the Controlled Microenvironment of a Colloidosome
Mann,Ellis,Twyman
, p. 4031 - 4037 (2016)
A water-soluble colloidosome composed of PGMA-PS latex was used as a microcapsule to host a catalyzed oxidation reaction within its dodecane core. When compared to a control reaction a significant colloidosome effect was observed. Specifically, a 233% increase in the relative yield of all products was observed for the colloidosome reaction. Furthermore, when the product distributions were calculated it was evident that a switch in selectivity had taken place. These studies showed there is a significant reduction in the relative yield of the epoxide product compared to the remaining oxidation products. Additional control experiments confirmed that rate enhancements were not simply a result of concentration and that reactions were not occurring in the outer latex phase. As a consequence of these control experiments, we suggest that the colloidosome enhancement and shift in product distribution, comes about from differences in electronic environment at or close to the interface between the internal oil phase and the outer colloidal particles. This environment is able to stabilize any specific intermediates and or transition states leading to enhanced reactions for these products and higher relative yields.
N?N Bond Formation Using an Iodonitrene as an Umpolung of Ammonia: Straightforward and Chemoselective Synthesis of Hydrazinium Salts
Tota, Arianna,Colella, Marco,Carlucci, Claudia,Aramini, Andrea,Clarkson, Guy,Degennaro, Leonardo,Bull, James A.,Luisi, Renzo
supporting information, p. 194 - 199 (2020/10/28)
The formation of hydrazinium salts by N?N bond formation has typically involved the use of hazardous and difficult to handle reagents. Here, mild and operationally simple conditions for the synthesis of hydrazinium salts are reported. Electrophilic nitrogen transfer to the nitrogen atom of tertiary amines is achieved using iodosylbenzene as oxidant and ammonium carbamate as the N-source. The resulting process is highly chemoselective and tolerant to other functional groups. A wide scope is reported, including examples with bioactive molecules. Insights on the structure of hydrazinium salts were provided by X-ray analysis. (Figure presented.).
CO2-activated NaClO-5H2O enabled smooth oxygen transfer to iodoarene: A highly practical synthesis of iodosylarene
Miyamoto, Kazunori,Watanabe, Yuichiro,Takagi, Taisei,Okada, Tomohide,Toyama, Takashi,Imamura, Shinji,Uchiyama, Masanobu
, (2021/05/27)
A safe, rapid, and environmentally friendly synthesis of iodosylarene (ArIO) has been developed using NaClO under a carbon dioxide (CO2) atmosphere. Exposure of iodoarene to NaClO-5H2O in acetonitrile under CO2 (1 atm) resulted in the clean formation of ArIO within 10 minutes in high yield. The absence of a base in this method enables the direct use of in-situ-generated iodosylarene not only for a variety of oxidative transformations (synthesis of sulfilimine, pentavalent bismuth, benzyne adduct, etc.), but also for the synthesis of iodonium ylide and imino-λ3-iodane in one pot.