Abstract

We report that Ru(bipy)3Cl2 can serve as a visible light photocatalyst for [2+2] enone cycloadditions. A variety of aryl enones participate readily in the reaction, and the diastereoselectivity in the formation of the cyclobutane products is excellent. We propose a mechanism in which a photogenerated Ru(bipy)3+ complex promotes one-electron reduction of the enone substrate, which undergoes subsequent radical anion cycloaddition. The efficiency of this process is extremely high, which allows rapid, high-yielding [2+2] cyclizations to be conducted using incident sunlight as the only source of irradiation.

Keywords

ChemistryEnonePhotocatalysisPhotochemistryCycloadditionCyclobutaneVisible spectrumSubstrate (aquarium)ArylCatalysisStereochemistryOrganic chemistryOptoelectronics

Affiliated Institutions

Related Publications

Photoredox Catalysis with Visible Light

Kirsten Zeitler

On the sunny side: Recent examples of visible-light-promoted photoredox catalysis in the presence of [Ru(bpy)3]2+ as an efficient photocatalyst have set new standards for conduc...

2009 Angewandte Chemie International Edition 973 citations

Photocatalysis and solar hydrogen production

Akihiko Kudo

Abstract Photocatalytic water splitting is a challenging reaction because it is an ultimate solution to energy and environmental issues. Recently, many new powdered photocatalys...

2007 Pure and Applied Chemistry 173 citations

Publication Info

Year
2008
Type
article
Volume
130
Issue
39
Pages
12886-12887
Citations
1097
Access
Closed

External Links

Download PDF (Free) View on DOI.org PubMed Semantic Scholar

Social Impact

Altmetric
PlumX Metrics

Social media, news, blog, policy document mentions

Citation Metrics

1097
OpenAlex
1
Influential
1061
CrossRef

Cite This

Michael A. Ischay, Mary E. Anzovino, Juana Du et al. (2008). Efficient Visible Light Photocatalysis of [2+2] Enone Cycloadditions. Journal of the American Chemical Society , 130 (39) , 12886-12887. https://doi.org/10.1021/ja805387f

Identifiers

DOI
10.1021/ja805387f
PMID
18767798

Data Quality

Data completeness: 77%