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Visible‐Light‐Mediated [4+2] Cycloaddition of Styrenes: Synthesis of Tetralin Derivatives
Author(s) -
Wang Leifeng,
Wu Fengjin,
Chen Jiean,
Nicewicz David A.,
Huang Yong
Publication year - 2017
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.201702940
Subject(s) - tetralin , cycloaddition , regioselectivity , styrene , yield (engineering) , steric effects , chemistry , catalysis , tricyclic , organic chemistry , photochemistry , materials science , copolymer , polymer , metallurgy
We report a formal [4+2] cycloaddition reaction of styrenes under visible‐light catalysis. Two styrene molecules with different electronic or steric properties were found to react with each other in good yield and excellent chemo‐ and regioselectivity. This reaction provides direct access to polysubstituted tetralin scaffolds from readily available styrenes. Sophisticated tricyclic and tetracyclic tetralin analogues were prepared in high yield and up to 20/1 diasteroselectivity from cyclic substrates.