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Photocatalytic Isomerization of Styrenyl Halides: Stereodivergent Synthesis of Functionalized Alkenes
Author(s) -
Zhang Hao,
Xu Qing,
Yu Lei,
Yu Shouyun
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201901119
Subject(s) - isomerization , chemistry , halide , stereospecificity , enyne , methanol , organic chemistry , combinatorial chemistry , photochemistry , catalysis
An efficient and general method for the isomerization of styrenyl halides under different photocatalytic conditions ( fac ‐Ir(ppy) 3 in methanol for E to Z isomerization and fluorescein in 1,4‐dioxane for Z to E isomerization, respectively) is disclosed. A series of stereospecific transformations constitute preliminary validation of this strategy in the synthesis of functionalized alkenes, including two diaryl alkenes, a styrenyl boronic ester and an enyne. The photocatalytic isomerization and subsequent cross coupling reaction can be run in a one‐pot manner. The stereodivergent synthesis of all four isomers of a conjugated diene, as well as the antitumor agent DMU‐212 and its ( Z )‐isomer highlights the synthetic applicability of this method.