Intermolecular 1,2‐Difunctionalization of Nitriles <i>via</i> Redox Gold Catalysis: Synthesis of Benzoxazoles and Benzimidazoles
The unprecedent gold-catalyzed intermolecular 1,2-difunctionalization of nitriles with o-iodophenols or o-iodoanilines via Au(I)/Au(III) redox catalysis has been developed, providing an expedient route to the synthesis of benzoxazoles or benzimidazoles with broad substrate scope and high functional compatibility. Mechanistic investigation reveals that the Au(III)-Ar species generated via oxidative addition of o-iodophenol to MeDalphosAu<sup>+</sup>, serves as a key intermediate. Particularly, this annulation is initiated by oxidative addition, rather than the nucleophilic attack of the phenol moiety in o-iodophenol towards the nitrile. The method was also applied to the synthesis of poly aza-heterocycles via a cascade Au(I)/Au(III) and Au(I) catalysis relay.
Authors
- Yuanhong Liu (ORCID: https://orcid.org/0000-0003-1153-5695)
- Zheng‐Yang Xu (ORCID: https://orcid.org/0000-0003-4605-8286)
- Yifeng Chen (ORCID: https://orcid.org/0000-0003-3239-6209)
- Ming Chen (ORCID: https://orcid.org/0000-0003-4957-2934)
- Chengzhi Xu
Institutions
- East China University of Science and Technology (CN)
- Shanghai Institute of Organic Chemistry (CN)
- Changzhou University (CN)
- State Key Laboratory of Organometallic Chemistry
Publication Details
- Journal
- Chemistry - A European Journal
- Published
- 2025-01-09
- DOI
- https://doi.org/10.1002/chem.202404368
- Citations
- 1
- Primary Topic
- Catalytic Alkyne Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.94
Funders
- National Natural Science Foundation of China
- Chinese Academy of Sciences
- Changzhou University
- National Key Research and Development Program of China