A [3 + 2] formal cycloaddition reaction using aza-oxyallyl cation as a synthetic synthon was developed to construct the pyrroloindololine core. With this novel method, a variety of C3-substituted indoles were readily converted into the corresponding pyrroloindoline analogues at room temperature in the mixed solvents. To further demonstrate the utility of this method, a synthetic approach to the total synthesis of (±)-minfiensine was developed in quite concise fashion.
A direct oxidative cyanation of arenes under Fe(II) catalysis with 3,5-di(trifluoromethyl)phenyl(cyano)iodonium triflate (DFCT) as the cyanating agent has been developed. The reaction is applicable to wide range of aromatic substrates, including polycyclic structures and heteroaromatic compounds.
We present the anhydride-based
decarboxylative alkylation of aryl
iodides catalyzed by nickel. This method of decarboxylative coupling
works with a broad scope of aliphatic carboxylic anhydrides and tolerates
synthetically useful aromatic substituents. Assisted by a redox system
of pyridine N-oxide and zinc additives, the current
reaction occurs under mild conditions and without the assistance of
photocatalyst. Notably, this method features high chemoselectivity
toward alkyl migration with mixed aliphatic/aromatic anhydrides. Thus,
it provides a powerful synthetic tool to modify high-valued aliphatic
carboxylic acids by converting them into mixed anhydrides using readily
available aryl carboxylic acids such as p-toluic
acid. We propose a catalytic cycle that involves the key steps of
free radical-based decarboxylation and subsequent alkyl transfer to
nickel that precedes an oxidatively induced C–C reductive elimination
from Ni(III).
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