ChemInform Abstract: BENZO‐Γ‐PYRONES. PART X. REACTION OF DERIVATIVES OF BENZO‐Γ‐PYRONE WITH HYDROXYLAMINE

Maib, P.; Jerzmanowska, Z.

doi:10.1002/chin.198401199

Cited by 1 publication

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“…To verify the computations, we compared them with experimental data. The experimentally determined soft atoms for compounds 1 ,29 9 24 and for the coumarins30–35 ( 21 – 23,25 ) agree well with the computations. Thus we can conclude here that the intermediate is a soft nucleophile (as most nucleophiles derived from heavy elements) and should therefore attack the softest atom in the substrate.…”

Section: Resultssupporting

confidence: 73%

Homogeneous hydrogenation of electron‐deficient alkenes by iridium complexes

Semeniuchenko

Exner

Khilya

et al. 2011

Applied Organom Chemis

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aThe catalytic homogeneous hydrogenation of electron-deficient alkenes (nucleophilic hydrogenation) was achieved in the presence of iridium complexes and a base as co-catalyst. Contrary to hydrogenation of electron-rich alkenes, which is inactivated by bases, the hydrogenation of the electron-deficient alkenes turned out to be base activated. Here, we present a more thorough study on the capacities but also limitations of this new reaction mechanism using screenings of the reaction conditions as well as different Ir complexes and substrates. The formation of a catalytically active Ir complex is proposed. The active complex usually attacks a soft electron-deficient atom, if more than one possibility exists (as shown by density functional theory computations). Additionally, first examples of enantiomeric enrichments in the presence of chiral Ir complexes are presented. The high catalyst load needed and the moderate yields show that the active complex is very unstable under conditions of nucleophilic hydrogenation and is quickly deactivated, which has to be addressed in further studies. Copyright

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Section: Resultssupporting

confidence: 73%