The weakly coordinating enaminone functionality has been leveraged for a C-H bond activation strategy under ruthenium catalysis and employed in the regioselective annulative coupling of arenes with diazonaphthoquinones, offering polycyclic benzocoumarins in very high yields. The enaminone motif plays a dual role and the protocol operates through a Ru(II)/Ru(IV) catalytic pathway which is amenable to the diversification of various pharmacophore-coupled substrates.
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Enaminone-directed ruthenium(II)-catalyzed C-H activation and annulation of arenes with diazonaphthoquinones for polycyclic benzocoumarins.
Chem Commun (Camb)
November 2023
Department of Chemistry, Indian Institute of Technology Madras, Chennai 600 036, Tamil Nadu, India.
The weakly coordinating enaminone functionality has been leveraged for a C-H bond activation strategy under ruthenium catalysis and employed in the regioselective annulative coupling of arenes with diazonaphthoquinones, offering polycyclic benzocoumarins in very high yields. The enaminone motif plays a dual role and the protocol operates through a Ru(II)/Ru(IV) catalytic pathway which is amenable to the diversification of various pharmacophore-coupled substrates.
View Article and Find Full Text PDFConstruction of C-C Axial Chirality via Asymmetric Carbene Insertion into Arene C-H Bonds.
Angew Chem Int Ed Engl
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Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, School of Petrochemical Engineering, Changzhou University, 1 Gehu Road, 213164, Changzhou, China.
By using diazonaphthoquinones and anilines as key reagents and through a point-to-axis chiral transfer strategy, the atroposelective synthesis via asymmetric C(sp )-H bond insertion reaction of arenes has been realized under rhodium catalysis, providing the resulting biaryl atropisomers in moderate to excellent yields with good enantiomeric ratios (up to 99:1). Further elaboration indicates this type of axially biaryl scaffold may have promising potentials in developing novel chiral ligands.
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