A novel Ru-catalyzed tandem C-H bond activation tool has been successfully developed involving allylation and oxidative cyclization of 2-phenyl indoles with allyl carbonates. This one-pot reaction is a new way to synthesize indolo[2,1-a]isoquinoline units via a simple and efficient process.
Versatile reactive activities of allyl alcohols with free indoles in C-H functionalization reactions were investigated. Direct alkylation or cascade cyclization reactions could be selectively controlled based on the catalyst system: Ru(PPh ) Cl provided C3-substituted β-ketone indoles whereas [Ru(p-cymene)Cl ] yielded cyclized indoles.
A highly efficient Ir -catalyzed cascade cyclization of indoles and diazoes giving access to unique pentacyclic-fused carbazoles has been developed. This novel strategy expanded the application scope of coupling partners to take diazo compounds as a C2 source, and two new cycles, three new C-C and one new C-N bonds were formed in one-pot.
Rhodium(iii)-catalyzed N-directed ortho C-H activation and subsequent roll-over C-H activation represents an important strategy to synthesize fused polycyclic compounds. Herein, the novel methodology broadens the scope of the coupling partner to alkenes, which working smoothly with 7-azaindoles has been proven to be an efficient and atom-economical strategy to access complex π-conjugated 7-azaindole derivatives.
A unified strategy for an efficient and high diastereoand enantioselective synthesis of (−)-chloramphenicol, (−)-azidamphenicol, (+)-thiamphenicol, and (+)-florfenicol based on a key catalytic syn-selective Henry reaction is reported. The stereochemistry of the ligand-enabled copper(II)-catalyzed aryl aldehyde Henry reaction of nitroethanol was first explored to forge a challenging syn-2-amino-1,3-diol structure unit with vicinal stereocenters with excellent stereocontrol. Multistep continuous flow manipulations were carried out to achieve the efficient asymmetric synthesis of this family of amphenicol antibiotics.
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