Exploring the Electronic and Steric Effects of Hemilabile (P^N) Ligands in Redox Gold Catalysis: Application to the Cross-Coupling Reaction of Aliphatic Amines with Aryl Iodides
Herein, we report 17 new (P^N) ligands for redox gold catalysis, featuring various substituents at -C4, -C5, and -C6 of the aryl ring and nitrogen handle. Rate kinetics experiments revealed that electron-rich substituents at -C4 and -C5 positions of the aryl ring enhanced the rate of oxidative addition of Au(I) with C(sp<sup>2</sup>)-Br bonds compared to electron-poor substituents. Further, we report an unprecedented gold-catalyzed arylation of aliphatic amines using an electronically rich ligand (<b>L6</b>) with an -OMe group at the -C5 position.
Authors
- Nitin T. Patil (ORCID: https://orcid.org/0000-0002-8372-2759)
- Saurabh Rai (ORCID: https://orcid.org/0000-0003-2923-0566)
- Gaurav Shukla (ORCID: https://orcid.org/0000-0002-1927-2095)
- Urvashi Urvashi (ORCID: https://orcid.org/0009-0000-2653-8085)
- Nisha Nisha
Institutions
- Indian Institute of Science Education and Research, Bhopal (IN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-02-28
- DOI
- https://doi.org/10.1021/acs.orglett.5c00203
- Citations
- 12
- Primary Topic
- Catalytic Alkyne Reactions
- Type
- article
- Field-Weighted Citation Impact
- 11.23
Funders
- Science and Engineering Research Board
- Board of Research in Nuclear Sciences