1315461-59-6Relevant articles and documents
Erratum: Synthesis of organic super-electron-donors by reaction of nitrous oxide with n-heterocyclic olefins (Journal of the American Chemical Society (2019) 141:43 (17112?17116) DOI: 10.1021/jacs.9b10660)
Eymann, Léonard Y. M.,Varava, Paul,Shved, Andrei M.,Curchod, Basile F. E.,Liu, Yizhu,Planes, Ophélie M.,Sienkiewicz, Andrzej,Scopelliti, Rosario,Fadaei Tirani, Farzaneh,Severin, Kay
, p. 1112 - 1112 (2020)
We realized that the legend of Figure S20 in the Supporting Information contains mistakes. The UV-vis spectrum of 5a was recorded at a lower concentration than indicated (0.023 mM instead of 0.06 mM), and the solvent used for the measurements was DMSO and not THF. The conclusions are not affected by this error. The Supporting Information has been corrected and is available.
Diazomethane umpolung atop anthracene: An electrophilic methylene transfer reagent
Joost, Maximilian,Transue, Wesley J.,Cummins, Christopher C.
, p. 1540 - 1543 (2018)
Formal addition of diazomethane's terminal nitrogen atom to the 9,10-positions of anthracene yields H2CN2A (1, A = C14H10 or anthracene). The synthesis of this hydrazone is reported from Carpino's hydrazine H2N2A through treatment with paraformaldehyde. Compound 1 has been found to be an easy-To-handle solid that does not exhibit dangerous heat or shock sensitivity. Effective umpolung of the diazomethane unit imbues 1 with electrophilicity at the methylene carbon center. Its reactivity with nucleophiles such as H2CPPh3 and N-heterocyclic carbenes is exploited for CC bond formation with elimination of dinitrogen and anthracene. Similarly, 1 is demonstrated to deliver methylene to a nucleophilic singlet d2 transition metal center, W(ODipp)4 (2), to generate the robust methylidene complex [2CH2]. This behavior is contrasted with that of the Wittig reagent H2CPPh3, a more traditional and Br?nsted basic methylene source that upon exposure to 2 contrastingly forms the methylidyne salt [MePPh3][2CH].
Using N-Heterocyclic Vinyl Ligands to Access Stable Divinylgermylenes and a Germylium Cation
Hering-Junghans, Christian,Andreiuk, Patricia,Ferguson, Michael J.,McDonald, Robert,Rivard, Eric
, p. 6272 - 6275 (2017)
Two efficient methods are presented to install σ- and π-electron-donating N-heterocyclic vinyl groups onto main-group elements (E): halosilane elimination and base-induced E?C bond formation. Placement of two NHC=CH? ligands (NHC=N-heterocyclic carbene) onto a GeII center affords a two-coordinate germylene, a heavy congener of the elusive divinyl carbenes. The π-donating ability of this vinylic ligand scaffold was further demonstrated by the synthesis of a three-coordinate germylium cation R3Ge+.
Highly regio- And stereoselective synthesis of cyclic carbonates from biomass-derived polyols: Via organocatalytic cascade reaction
Zhou, Hui,Zhang, Hui,Mu, Sen,Zhang, Wen-Zhen,Ren, Wei-Min,Lu, Xiao-Bing
supporting information, p. 6335 - 6341 (2019/12/03)
The cascade reaction of CO2, vicinal diols, and propargylic alcohol, was firstly achieved by dual Lewis base (LB) organocatalytic systems involving LB-CO2 adducts and commercially available organic amines. This methodology could overcome the chemical inertness of CO2, providing an alternative route to various functionalized five-membered cyclic carbonates in moderate to high yields under mild reaction conditions (25 °C, 1.0 atm of CO2). More importantly, this method could also be applied for facile and efficient synthesis of chiral polycyclic carbonates from biomass-derived polyols with complete configuration retention of chiral centers. This study provides an environment-friendly, scalable and cost effective protocol to construct value-added cyclic carbonates with multi-functional groups and chiral centers.
