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Intermolecular Dearomatization of Naphthalene Derivatives by Photoredox‐Catalyzed 1,2‐Hydroalkylation.
- Source :
-
Angewandte Chemie International Edition . 10/5/2020, Vol. 59 Issue 41, p18062-18067. 6p. - Publication Year :
- 2020
-
Abstract
- An intermolecular hydroalkylative dearomatization of naphthalenes with commercially available α‐amino acids is achieved via visible‐light photoredox catalysis. With an organic photocatalyst, a series of multi‐substituted 1,2‐dihydronaphthalenes are obtained in good‐to‐excellent yields. Intriguingly, by tuning the substituents at the C2 position of naphthalenes, formal dearomative [3+2] cycloadditions occur exclusively via a hydroalkylative dearomatization–cyclization sequence. This overall redox‐neutral method features mild reaction conditions, good tolerance of functionalities, and operational simplicity. Diverse downstream elaborations of the products are demonstrated. Preliminary mechanistic studies suggest the involvement of a radical–radical coupling pathway. [ABSTRACT FROM AUTHOR]
- Subjects :
- *NAPHTHALENE
*NAPHTHALENE derivatives
*CATALYSIS
*RING formation (Chemistry)
Subjects
Details
- Language :
- English
- ISSN :
- 14337851
- Volume :
- 59
- Issue :
- 41
- Database :
- Academic Search Index
- Journal :
- Angewandte Chemie International Edition
- Publication Type :
- Academic Journal
- Accession number :
- 146119394
- Full Text :
- https://doi.org/10.1002/anie.202008358