Divergent Mechanistic Scenarios for the C−sp2 and C−sp3 C−H Insertion of Aurated Aryl Cations-Reference-Cited by-同舟云学术

Divergent Mechanistic Scenarios for the C−sp² and C−sp³ C−H Insertion of Aurated Aryl Cations

Published:2023-08-23 Issue:19 Volume:365 Page:3320-3327
ISSN:1615-4150
Container-title:Advanced Synthesis & Catalysis
language:en
Short-container-title:Adv Synth Catal

Author:

Bucher Janina¹,Wurm Thomas¹,Farshadfar Kaveh²,Schukin Michael¹,Uzunidis Georgios¹,Rudolph Matthias¹,Rominger Frank¹,Ariafard Alireza³⁴,Hashmi A. Stephen K.¹⁵^ORCID

Affiliation:

1. Organisch-Chemisches Institut Heidelberg University Im Neuenheimer Feld 270 69120 Heidelberg Germany

2. Department of Chemistry and Material Science School of Chemical Engineering, Aalto University Kemistintie 1 02150 Espoo Finland

3. School of Physical Sciences University of Tasmania Private Bag 75 Hobart TAS 7001 Australia

4. Research School of Chemistry The Australian National University Canberra, ACT Australia

5. Chemistry Department Faculty of Science King Abdulaziz University (KAU) Jeddah 21589 Saudi-Arabia

Abstract

AbstractBy employing the sterically highly demanding steering ligand IPr* at a gold(I) center, it is possible to induce a 6‐endo‐dig cyclization pathway in 1,5‐diynes bearing terminal alkyne moieties. The resulting aurated naphthyl cations are utilized for the intermolecular formation of C−C bonds via C−H insertion of aromatic and aliphatic C−H bonds. The mechanisms of these transformations were studied by quantum chemical calculations.

Publisher

Wiley

Subject

Organic Chemistry,Catalysis

Link

https://onlinelibrary.wiley.com/doi/pdf/10.1002/adsc.202300548

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