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oxetanes July 8th.pdf (1.3 MB)

Visible Light-Enabled Paternò-Büchi Reaction via Triplet Energy Transfer for the Synthesis of Oxetanes

preprint
revised on 08.07.2020 and posted on 09.07.2020 by Katie Rykaczewski, Corinna Schindler

One of the most efficient ways to synthesize oxetanes is the light-enabled [2+2] cycloaddition reaction of carbonyls and alkenes, referred to as the Paternò-Büchi reaction. The reaction conditions for this transformation typically require the use of high energy UV light to excite the carbonyl, limiting the applications, safety, and scalability. We herein report the development of a visible light-mediated Paternò-Büchi reaction protocol that relies on triplet energy transfer from an iridium-based photocatalyst to the carbonyl substrates. This mode of activation is demonstrated for a variety of aryl glyoxylates and negates the need for both, visible light-absorbing carbonyl starting materials or UV light to enable access to a variety of functionalized oxetanes in up to 99% yield.


History

Email Address of Submitting Author

corinnas@umich.edu

Institution

University of Michigan

Country

United States

ORCID For Submitting Author

0000-0003-4968-8013

Declaration of Conflict of Interest

No conflict of interest

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