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Olefin‐Supported Cationic Copper Catalysts for Photochemical Synthesis of Structurally Complex Cyclobutanes
Author(s) -
Gravatt Christopher S.,
MelecioZambrano Luis,
Yoon Tehshik P.
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202013067
Subject(s) - cyclobutanes , cyclobutane , catalysis , chemistry , cationic polymerization , alkene , steric effects , olefin fiber , photochemistry , reactivity (psychology) , cyclopentene , cyclohexene , organic chemistry , cycloaddition , ring (chemistry) , medicine , alternative medicine , pathology
The sole method available for the photocycloaddition of unconjugated aliphatic alkenes is the Cu‐catalyzed Salomon–Kochi reaction. The [Cu(OTf)] 2 ⋅benzene catalyst that has been standard in this reaction for many decades, however, is air‐sensitive, prone to photodecomposition, and poorly reactive towards sterically bulky alkene substrates. Using bench‐stable precursors, an improved catalyst system with superior reactivity and photostability has been designed, and it offers significantly expanded substrate scope. The utility of this new catalyst for the preparation of sterically crowded cyclobutane structures is highlighted through the preparation of the cores of the natural products sulcatine G and perforatol.