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Search for "π-acid" in Full Text gives 8 result(s) in Beilstein Journal of Organic Chemistry.
Methodologies for the synthesis of quaternary carbon centers via hydroalkylation of unactivated olefins: twenty years of advances
Beilstein J. Org. Chem. 2021, 17, 1565–1590, doi:10.3762/bjoc.17.112
- expense of the olefin double bond. Review Olefin activation by transition metals Transition metals can act as π-acid catalysts in olefin double bond activation, as they weaken the alkene double bond through coordination to allow a nucleophilic attack on the sp2 carbon to form an alkylmetal intermediate
Fluorohydration of alkynes via I(I)/I(III) catalysis
Beilstein J. Org. Chem. 2020, 16, 1627–1635, doi:10.3762/bjoc.16.135
- fluorination of acetophenone derivatives was achieved using iodosylarenes and commercially available NEt3/HF 1:5 to generate the ArIF2 species in situ is also highly pertinent [39][40] (Figure 1A). Elegant reports describing the conversion of internal alkynes to α-fluoroketones via π-acid catalysis were also
Harnessing enzyme plasticity for the synthesis of oxygenated sesquiterpenoids
Beilstein J. Org. Chem. 2019, 15, 2184–2190, doi:10.3762/bjoc.15.215
- , the presence of an ethereal oxygen atom containing π-acid functionality alongside its inductive withdrawal effect has a profound effect on the carbocationic reactivity of the intermediates. Of course a fully comprehensive interpretation of these results, regarding potentially interesting aspects such
Chiral cyclopentadienylruthenium sulfoxide catalysts for asymmetric redox bicycloisomerization
Beilstein J. Org. Chem. 2016, 12, 1136–1152, doi:10.3762/bjoc.12.110
- bicycloisomerization reaction (vide infra). Unlike ruthenium and palladium enyne cycloisomerization, which operate via metallacycle formation or hydrometallation, gold acts as a π-acid, increasing the electrophilicity of the alkyne by η2 coordination. The pendant alkene cyclizes on the alkyne, and the resulting
Catalytic asymmetric synthesis of biologically important 3-hydroxyoxindoles: an update
Beilstein J. Org. Chem. 2016, 12, 1000–1039, doi:10.3762/bjoc.12.98
- spirocyclic 2,5-dihydrofuran was obtained in 98% yield when the π acid AuCl3 (5 mol %) was used. AuCl3 may coordinate one of the allene double bonds via a monodentate model. The phenol substrate did not participate in this reaction. In 2013, Ji and co-workers described the I2-catalyzed construction of pyrrolo
Ambient gold-catalyzed O-vinylation of cyclic 1,3-diketone: A vinyl ether synthesis
Beilstein J. Org. Chem. 2013, 9, 2537–2543, doi:10.3762/bjoc.9.288
- addition to the alkyne besides the typical π-acid activation [12][13][14][15][16][17]. Our group has developed the 1,2,3-triazole coordinated gold complexes (TA-Au) as stable catalysts for alkyne activation in the past several years [26][27][28][29][30]. Considering that TA-Au complexes might have
Synthesis of a novel chemotype via sequential metal-catalyzed cycloisomerizations
Beilstein J. Org. Chem. 2012, 8, 1338–1343, doi:10.3762/bjoc.8.153
- diversity; cycloisomerization; cyclopropane; diyne; isochromene; π-acid; Introduction Our laboratory has an ongoing interest in discovering transformations that afford novel chemotypes [1][2][3][4]. To this end, we have developed a reaction screening paradigm that enables the discovery of new reaction
Isotopic labelling studies for a gold-catalysed skeletal rearrangement of alkynyl aziridines
Beilstein J. Org. Chem. 2011, 7, 839–846, doi:10.3762/bjoc.7.96
- other reports into π-acid promoted alkynyl aziridine cycloisomerisations without skeletal rearrangement [20][21][22][23]. Our working mechanism to explain this reaction divergence centred on the electrophilic activation of the alkyne in A triggering a ring-expansion to a common intermediate B from which
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