Aqueous Amine-Tolerant [2+2] Photocycloadditions of Unactivated Olefins

The Kochi–Salomon reaction is the only photochemical [2+2] cycloaddition capable of combining two electronically unactivated olefins into a cyclobutane. Yet, the reaction has remained largely unexplored and suffers many drawbacks, most notably an intolerance to Lewis/Brønsted basic amines and amides...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 144; no. 43; pp. 19689 - 19694
Main Authors Mansson, Carl M. F., Burns, Noah Z.
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 02.11.2022
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
PHOTOBICYCLIZATION
OXIDATION
CYCLOADDITIONS
STEREOSELECTIVE-SYNTHESIS
SCAFFOLDS
COPPER(I) CATALYSIS
DISCOVERY
PHOTOREACTIONS
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Summary:The Kochi–Salomon reaction is the only photochemical [2+2] cycloaddition capable of combining two electronically unactivated olefins into a cyclobutane. Yet, the reaction has remained largely unexplored and suffers many drawbacks, most notably an intolerance to Lewis/Brønsted basic amines and amides. Since these groups are ubiquitous in biologically active pharmaceuticals, an amine-tolerant Kochi–Salomon reaction would greatly facilitate rapid exploration of novel drug scaffolds. Herein, we disclose a transformation that is run in water with the most widely available Cu­(II) salts and mineral acids. Furthermore, we apply this methodology to synthesize a variety of amine-containing cyclobutanes, including known and novel pharmacological analogues.
Bibliography:ObjectType-Article-1
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ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.2c08778