Publication

TiCl<sub>3</sub>-Mediated Reductive Aminohydroxylation of Alkenes to (Benzo)Furo[3,2-<i>b</i>]Indolines

2026

Abstract

We report a TiCl 3-mediated reductive double cyclization of ortho-nitroaryl-substituted styrene and stilbene derivatives that enables efficient access to dihydrofuro[3,2-b]indolines and benzofuro[3,2b]indolines under mild conditions. The transformation proceeds through a single-electron transfer (SET) reduction of the nitro group to a nitroso intermediate, followed by a concerted 5-center, 6π-electrocyclization to generate a nitrone. Intramolecular trapping of this nitrone by a tethered hydroxy or phenol group forms a cyclic hydroxylamine, which undergoes further SET reduction to furnish the fused indoline products. This domino reductive cascade provides a mechanistically distinct and complementary alternative to established oxidative methods for constructing [3,2-b] fused indoline architectures.

Official source

https://infoscience.epfl.ch/entities/publication/bea167d5-eff6-415f-bd4d-e8397d578e5a

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2026

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/bea167d5-eff6-415f-bd4d-e8397d578e5a

About this result

Related concepts (24)

Phenols

In organic chemistry, phenols, sometimes called phenolics, are a class of chemical compounds consisting of one or more hydroxyl groups (−OH) bonded directly to an aromatic hydrocarbon group. The simplest is phenol, C6H5OH. Phenolic compounds are classified as simple phenols or polyphenols based on the number of phenol units in the molecule. Phenols are both synthesized industrially and produced by plants and microorganisms. Phenols are more acidic than typical alcohols.

Nitrile

In organic chemistry, a nitrile is any organic compound that has a functional group. The prefix cyano- is used interchangeably with the term nitrile in industrial literature. Nitriles are found in many useful compounds, including methyl cyanoacrylate, used in super glue, and nitrile rubber, a nitrile-containing polymer used in latex-free laboratory and medical gloves. Nitrile rubber is also widely used as automotive and other seals since it is resistant to fuels and oils.

Nitro compound

In organic chemistry, nitro compounds are organic compounds that contain one or more nitro functional groups (). The nitro group is one of the most common explosophores (functional group that makes a compound explosive) used globally. The nitro group is also strongly electron-withdrawing. Because of this property, bonds alpha (adjacent) to the nitro group can be acidic. For similar reasons, the presence of nitro groups in aromatic compounds retards electrophilic aromatic substitution but facilitates nucleophilic aromatic substitution.