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Novel regioselective hydrodeoxygenation of α-diketones with phosphites as the deoxygenation reagent was realized via visible-light photoredox catalysis. Broad substrate scope and high functional group compatibility were obtained. Unsymmetric α-diketones were selectively reduced at the carbonyls of higher electrophilicity. This unique regioselectivity compared with available methods makes it a practical complementary approach for the monohydrodeoxygenation of α-diketones.
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http://dx.doi.org/10.1021/acs.orglett.3c02936 | DOI Listing |
ACS Sustain Chem Eng
August 2025
Instituto de Tecnología Química (UPV-CSIC), Universitat Politècnica de València-Consejo Superior de Investigaciones Científicas, Av. de los Naranjos s/n, València 46022, Spain.
The development of efficient and sustainable methods for producing azalactams, pivotal compounds in medicinal chemistry, is a relevant topic in fine chemistry. Here, we present a heterogeneous catalytic protocol to synthesize azaisoindolinones via the hydro-deoxygenation of azaphthalimides, producing water as the only byproduct. Notably, the [AgRe/AlO] nanocatalyst promotes the desired transformation, showing full tolerance to the pyridine ring, a substantial improvement in heterogeneous catalysis, and total regioselectivity.
View Article and Find Full Text PDFOrg Lett
October 2023
Key Laboratory of Natural Medicine and Immune Engineering, School of Pharmacy, Henan University, Kaifeng 475004, People's Republic of China.
Novel regioselective hydrodeoxygenation of α-diketones with phosphites as the deoxygenation reagent was realized via visible-light photoredox catalysis. Broad substrate scope and high functional group compatibility were obtained. Unsymmetric α-diketones were selectively reduced at the carbonyls of higher electrophilicity.
View Article and Find Full Text PDFACS Appl Mater Interfaces
January 2020
Department of Chemical and Biological Engineering , University of Colorado, Boulder , Boulder , Colorado 80309 , United States.
Amphiphilic Janus particles with a catalyst selectively loaded on either the hydrophobic or hydrophilic region are promising candidates for efficient and phase-selective interfacial catalysis. Here, we report the synthesis and characterization of Janus silica particles with a hydrophilic silica domain and a silane-modified hydrophobic domain produced via a wax masking technique. Palladium nanoparticles were regioselectively deposited on the hydrophobic side, and the phase selectivity of the catalytic Janus particles was established through the kinetic studies of benzyl alcohol hydrodeoxygenation (HDO).
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