C À H activation-based ring-forming methods are Scheme 1. Previous work, working mechanistic hypothesis to design our enantioselective synthesis of fluoradenes and target molecules.
Global drive away from fossil feedstock requires the
development
of synthetic procedures to enhance the efficiency of CO2 capture and utilization processes using renewable starting materials
and catalysts. Here, we report an alternative reaction pathway for
the O-formylation of alcohols and bio-alcohols, which
affords industrially relevant formate esters. Most products, reported
herein, derive their carbon atoms exclusively from renewable sources.
The reaction is catalyzed by formic acid, which can also be produced
directly from CO2 captured in the reaction. The resulting
in situ produced formic acid improves the reaction rate, with each
catalyst recycling by simple filtration, product distillation, and
reuse of the residual reaction mixture. Hence, CO2 is used
as a C1 building block and simultaneously reduced to formic acid,
which in turn autocatalytically promotes the reaction.
C−H activation‐based ring‐forming methods are a powerful approach for the construction of complex molecular architectures, especially those containing a congested stereocenter. Therefore, this strategy seems perfectly suited to address the synthesis of chiral polycyclic aromatic hydrocarbons (PAHs) and bowl‐shaped molecules, which are important target molecules in the field of organic electronic materials. Herein, we describe an enantioselective Pd0‐catalyzed C(sp2)−H arylation protocol for the synthesis of chiral fluoradenes and other warped molecules, which could serve to the bottom‐up construction of chiral PAHs. The current approach relies on the use of chiral bifunctional phosphine–carboxylate ligands and delivers diverse polycyclic compounds in high yield and with good to excellent enantioselectivity. The chiroptical properties of the obtained products were investigated, and some of them were found to have a strong ellipticity and an emission band located in the visible region.
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