49769-78-0Relevant articles and documents
Reaction of dicarbomethoxycarbene with thiophene derivatives
Jenks, William S.,Heying, Melanie J.,Stoffregen, Stacey A.,Rockafellow, Erin M.
, p. 2765 - 2770 (2009)
Photolysis of derivatives of dimethylmalonate thiophene-S,C-ylide provides dicarbomethoxycarbene, which can react with thiophene to form dimethyl (2-thienyl)malonate. By generation of dicarbomethoxycarbene from the dibenzothiophene-based ylide in neat thi
Reductive Knoevenagel Condensation with the Zn-AcOH System
Ivanov, Konstantin L.,Melnikov, Mikhail Ya.,Budynina, Ekaterina M.
, p. 1285 - 1291 (2020/11/13)
An efficient gram-scale one-pot approach to 2-substituted malonates and related structures is developed, starting from commercially available aldehydes and active methylene compounds. The technique combines Knoevenagel condensation with the reduction of the C=C bond in the resulting activated alkenes with the Zn-AcOH system. The relative ease with which the C=C bond reduction occurs can be traced to the accepting abilities of the substituents in the intermediate arylidene malonates.
Au-Cavitand Catalyzed Alkyne-Acid Cyclizations
Ho, Tam D.,Schramm, Michael P.
supporting information, p. 5678 - 5684 (2019/08/21)
Supramolecular cavitands that contain inwardly directed functional groups have yielded specialized transformations and trapping of reactive intermediates. A recently reported 3-wall Au cavitand provides exciting opportunities for supramolecular catalysis. In this study, a variety of substituted γ-alkynoic acids were reacted to give lactones. The interaction of peripheral “R” groups revealed differential catalyst behavior. Extremely large and small groups reacted with appreciable rate. Intermediate sized groups however, slowed significantly: giving support that size-specific binding is at play when using cavitands as a scaffold for gold catalysis. These results serve as some of the first evidence of the interplay between substrate and cavitand interior in the catalytic sphere.
Intermolecular Reductive Couplings of Arylidene Malonates via Lewis Acid/Photoredox Cooperative Catalysis
McDonald, Benjamin R.,Scheidt, Karl A.
supporting information, p. 6877 - 6881 (2018/11/02)
A cooperative Lewis acid/photocatalytic reduction of arylidene malonates yields a versatile radical anion species. This intermediate preferentially undergoes intermolecular radical-radical coupling reactions, and not the conjugate addition-dimerization reactivity typically observed in the single-electron reduction of conjugate acceptors. Reported here is the development of this open-shell species in intermolecular radical-radical cross couplings, radical dimerizations, and transfer hydrogenations. This reactivity underscores the enabling modularity of cooperative catalysis and demonstrates the utility of stabilized enoate-derived radical anions in intermolecular bond forming reactions.
