2039-68-1Relevant articles and documents
Direct Conversion of Alcohols into Alkenes by Dehydrogenative Coupling with Hydrazine/Hydrazone Catalyzed by Manganese
Das, Uttam Kumar,Chakraborty, Subrata,Diskin-Posner, Yael,Milstein, David
supporting information, p. 13444 - 13448 (2018/09/14)
We have developed unprecedented methods for the direct transformation of primary alcohols to alkenes in the presence of hydrazine, and for the synthesis of mixed alkenes by the reaction of alcohols with hydrazones. The reactions are catalyzed by a manganese pincer complex and proceed in absence of added base or hydrogen acceptors, liberating dihydrogen, dinitrogen, and water as the only byproducts. The proposed mechanism, based on preparation of proposed intermediates and control experiments, suggests that the transformation occurs through metal–ligand cooperative N?H activation of a hydrazone intermediate.
Redesign of a Pyrylium Photoredox Catalyst and Its Application to the Generation of Carbonyl Ylides
Alfonzo, Edwin,Alfonso, Felix Steven,Beeler, Aaron B.
supporting information, p. 2989 - 2992 (2017/06/07)
We report the exploration into photoredox generation of carbonyl ylides from benzylic epoxides using newly designed 4-mesityl-2,6-diphenylpyrylium tetrafluoroborate (MDPT) and 4-mesityl-2,6-di-p-tolylpyrylium tetrafluoroborate (MD(p-tolyl)PT) catalysts. These catalysts are excited at visible wavelengths, are highly robust, and exhibit some of the highest oxidation potentials reported. Their utility was demonstrated in the mild and efficient generation of carbonyl ylides from benzylic epoxides that otherwise could not be carried out by current common photoredox catalysts.
Reductive coupling of aldehydes by H2S in aqueous solutions, a C-C bond forming reaction of prebiotic interest
Kajjout, Mohammed,Hebting, Yanek,Albrecht, Pierre,Adam, Pierre
experimental part, p. 714 - 726 (2012/07/14)
We report here a novel reductive coupling reaction of conjugated, non- or poorly enolizable aldehydes induced by H2S and operative in aqueous solutions under prebiotically relevant conditions. This reaction leads from retinal to β-carotene, and from benzylic aldehydes to the corresponding diarylethylenes. This novel reaction also opens a new potentially prebiotic pathway leading from glyoxylic acid to various compounds that are involved in the reductive tricarboxylic acid cycle. This C-C bond forming reaction of prebiotic interest might have been operative, notably, in the sulfide-rich environments of hydrothermal vents, which have been postulated as possible sites for the first steps of organic chemical evolution.