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Lignin is an aromatic polymer that constitutes up to 30 wt% of woody biomass and is considered the largest source of renewable aromatics. Valorization of the lignin stream is pivotal for making biorefining sustainable. Monomeric units in lignin are bound via C–O and C–C bonds. The majority of existing methods for the production of valuable compound...
The direct intramolecular stereospecific substitution of the hydroxyl group in enantiomerically enriched secondary benzylic, allylic, propargylic, and alkyl alcohols was successfully accomplished by phosphinic acid catalysis. The hydroxyl group was displaced by O-, S-, and N-centered nucleophiles to provide enantioenriched five-membered tetrahydrof...
Chiral α-sulfenylated ketones are versatile building blocks, although there are still several limitations with their prep-aration. Here we report a new two-step procedure, consisting in a Pd-catalyzed hydrothiolation of propargylic alco-hols followed by an enantioselective Rh-isomerization of allylic alcohols. The isomerization reaction is the key...
Non-activated phenols have been employed as nucleophiles in the allylation of non-derivatized allylic alcohols to generate allylated phenolic ethers with water as the only by-product. A Pd[BiPhePhos] catalyst was found to be reactive to give the O-allylated phenols in good to excellent yields in the presence of molecular sieves. The reactions are c...
A series of 2,3-diarylindoles were synthesized via the Larock heteroannulation, and evaluated for their anticancer activity against A549 lung cancer cells. The most potent compound, PCNT13 with IC50=5.17μM, caused the induction of two modes of programmed cell death, apoptosis and autophagy.
A series of 2,3-diarylindoles were synthesized from 2-iodoaniline and unsymmetrical diarylacetylenes using the Larock heteroannulation. Diarylacetylenes bearing electron-withdrawing substituents lead to 2,3-diarylindoles with substituted phenyl moieties at the 2-position as major products, while those with electron-donating groups preferably yield...