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Construction of Cyclobutanes by Multicomponent Cascade Reactions in Homogeneous Solution through Visible‐Light Catalysis
Author(s) -
Lei Tao,
Zhou Chao,
Wei XiangZhu,
Yang Bing,
Chen Bin,
Tung ChenHo,
Wu LiZhu
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201804946
Subject(s) - cyclobutanes , photochemistry , chemistry , cycloaddition , catalysis , ylide , aldehyde , cyclobutane , aldol reaction , ketone , organic chemistry , ring (chemistry)
[2+2] Photocycloaddition of two olefins is a general method to assemble the core scaffold, cyclobutane, found in numerous bioactive molecules. A new approach to synthesize cyclobutanes through multicomponent cascade reactions by merging aldol reaction and Witting reaction with visible‐light‐induced [2+2] cycloaddition is reported. An array of cyclobutanes with high selectivity has been achieved from commercially available aldehydes, ketones (or phosphorus ylide), and olefins with visible‐light irradiation of a catalytic amount of ( fac ‐tris(2‐phenylpyridinato‐C 2 ,N)iridium) ([Ir(ppy) 3 ]) at room temperature. Control experiments and spectroscopic studies revealed that the triplet–triplet energy transfer from the excited [Ir(ppy) 3 ]* to enones, generated in situ from aldehyde and ketone or aldehyde and phosphorus ylide, is responsible for these simple and efficient muticomponent transformations.