Photocatalytic Isomerization of Styrenyl Halides: Stereodivergent Synthesis of Functionalized Alkenes. Issue 10 (26th September 2019)

• Record Type: Journal Article
• Authors: Zhang, Hao; Xu, Qing; Yu, Lei; Yu, Shouyun
• Other Names: Masson Géraldine guestEditor.; König Burkhard guestEditor.; Yoon Tehshik guestEditor.
• Is Part Of: European journal of inorganic chemistry. Issue 10(2020)
• Page Start: 1472
• Page End: 1477
• Publication Date: 2019-09-26
• Subjects: Alkenes -- Styrenyl halides -- Isomerization -- Photocatalysis; Chemistry, Inorganic -- Periodicals; Organometallic chemistry -- Periodicals; Bioinorganic chemistry -- Periodicals; Solid state chemistry -- Periodicals; 546
• DOI: 10.1002/ejoc.201901119
• Languages: English
• ISSNs: 1434-1948

Abstract

Abstract : 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. Abstract : An efficient and general method for the isomerization of styrenyl halides under photocatalytic conditions is reported. 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.