29414-55-9Relevant articles and documents
A Dinickel Catalyzed Cyclopropanation without the Formation of a Metal Carbene Intermediate
Maity, Arnab K.,Kalb, Annah E.,Zeller, Matthias,Uyeda, Christopher
supporting information, p. 1897 - 1902 (2020/11/30)
(NDI)Ni2 catalysts (NDI=naphthyridine-diimine) promote cyclopropanation reactions of 1,3-dienes using (Me3Si)CHN2. Mechanistic studies reveal that a metal carbene intermediate is not part of the catalytic cycle. The (NDI)Ni2(CHSiMe3) complex was independently synthesized and found to be unreactive toward dienes. Based on DFT models, we propose an alternative mechanism that begins with a Ni2-mediated coupling of (Me3Si)CHN2 and the diene. N2 extrusion followed by radical C?C bond formation generates the cyclopropane product. This model reproduces the experimentally observed regioselectivity and diastereoselectivity of the reaction.
Sustainable catalytic epoxidation of biorenewable terpene feedstocks using H2O2as an oxidant in flow microreactors
Bull, Steven D.,Cunningham, William B.,Plucinski, Pawel,Tibbetts, Joshua D.,Vezzoli, Massimiliano
supporting information, p. 5449 - 5455 (2021/08/16)
Solvent-free continuous flow epoxidation of the alkene bonds of a range of biorenewable terpene substrates have been carried out using a recyclable tungsten-based polyoxometalate phase transfer catalyst and aqueous H2O2 as a benign oxidant. These sustainable flow epoxidation reactions are carried out in commercial microreactors containing static mixing channels that enable common monoterpenes (e.g. untreated crude sulfate turpentine, limonene, etc.) to be safely epoxidized in short reaction times and in good yields. These flow procedures are applicable for the flow epoxidation of trisubstituted and disubstituted alkenes for the safe production of multigram quantities of a wide range of epoxides. This journal is
Synthetic studies on keramaphidin B: Formation of a macrocyclic ring by intramolecular Diels-Alder reaction
Nakada, Masahisa,Sekine, Daisuke,Shibata, Takahiro,Shimoda, Hiroki
, p. 3 - 11 (2020/01/28)
The possibility of constructing the macrocyclic ring of keramaphidin B via an intramolecular Diels-Alder (IMDA) reaction has been investigated. The IMDA reaction of a substrate possessing dihydropyridone and diene moieties, which were tethered by an alkyl chain including a linear triple bond, was found to proceed in the presence of SnCl4 at 80 °C.