Aminoarylation of Alkynes using Diarylanilines DOI Creative Commons

Zi Liu,

Michael F. Greaney

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(49), P. 6296 - 6299

Published: Jan. 1, 2024

Intermolecular aminoarylation of alkynes is described,

Language: Английский

Aryne‐Enabled C−N Arylation of Anilines DOI Creative Commons
Thomas Sephton, Anastasios Charitou, Cristina Trujillo

et al.

Angewandte Chemie, Journal Year: 2023, Volume and Issue: 135(49)

Published: Oct. 18, 2023

Abstract Anilines are potentially high‐value arylating agents, but limited by the low reactivity of strong C−N bond. We show that reactive intermediate benzyne can be used to both activate anilines, and set‐up an aryl transfer reaction in a single step. The does not require any transition metal catalysts or stoichiometric organometallics, establishes metal‐free route valuable biaryl products functionalizing aniline

Language: Английский

Citations

2
Asymmetric, Remote C(sp3)−H Arylation via Sulfinyl‐Smiles Rearrangement DOI Creative Commons
Yawen Hu, Cédric Hervieu, Estı́baliz Merino

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(17)

Published: March 20, 2024

Abstract An efficient asymmetric remote arylation of C(sp 3 )−H bonds under photoredox conditions is described here. The reaction features the addition radicals to a double bond followed by site‐selective radical translocation (1, n ‐hydrogen atom transfer) as well stereocontrolled aryl migration via sulfinyl‐Smiles rearrangement furnishing wide range chiral α ‐arylated amides with up >99 : 1 er. Mechanistic studies indicate that sulfinamide group governs stereochemistry product being rate determining step preceded kinetically favored 1, ‐HAT process.

Language: Английский

Citations

0
XAT‐Catalysis for Intramolecular Biaryl Synthesis DOI Creative Commons
Thomas Sephton,

Jonathan M. Large,

Louise S. Natrajan

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(35)

Published: May 31, 2024

Abstract Radical ipso‐ substitution offers an alternative to organometallic approaches for biaryl synthesis, but usually requires stoichiometric reagents such as tributyltin hydride. Here, we demonstrate that visible light photoredox catalysis can be used ipso ‐biaryl via a halogen‐atom transfer (XAT) regime. Using amide substrates promote over unwanted ortho‐ addition, smooth formation with no constraint on the electronic character of migrating arene ring. The photoreaction combined in one operation achieve formal arylation inert aniline C−N bond.

Language: Английский

Citations

0
Complexity-Generating Transformations Enabled by Intramolecular Radical Migration: Alkyl–Arylation of Simple Olefins DOI Creative Commons

Dylan J. Babcock,

Jaxon L. Barney,

Andrew J. Wolfram

et al.

Published: Aug. 9, 2023

A free-radical cascade approach has enabled the develop-ment of a synthetically versatile alkyl–arylation olefins. This transformation engages an excellent range olefins, from mono- to tetrasubstituted, without requiring directing or electronically activating groups. Further synthetic advantages, such as facile generation quaternary cen-ters and introduction heteroaryl groups with Lewis basic nitrogen atoms, also complement transition-metal-catalyzed alkyl–arylation. Vicinal stereoarrays were gener-ated high levels diastereoselectivity. The potential this was demonstrated by serving key step in concise synthesis oliceridine, new painkiller that received FDA approval 2020.

Language: Английский

Citations

1
Aminoarylation of Alkynes using Diarylanilines DOI Creative Commons

Zi Liu,

Michael F. Greaney

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(49), P. 6296 - 6299

Published: Jan. 1, 2024

Intermolecular aminoarylation of alkynes is described,

Language: Английский

Citations

0