- Photocatalytic Isomerization of Styrenyl Halides: Stereodivergent Synthesis of Functionalized Alkenes
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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.
- Zhang, Hao,Xu, Qing,Yu, Lei,Yu, Shouyun
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supporting information
p. 1472 - 1477
(2019/11/03)
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- Fritsch-Buttenberg-Wiechell rearrangement to alkynes from gem-dihaloalkenes with lanthanum metal
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The first example of the FBW rearrangement using of lanthanum metal and a catalytic amount of iodine was disclosed. When gem-diiodo- and gem-dibromoalkenes were treated with lanthanum metal in the presence of a catalytic amount of iodine, the reductive dehalogenation of these compounds smoothly proceeded to produce the corresponding alkynes in moderate to good yields.
- Umeda, Rui,Yuasa, Takumi,Anahara, Namika,Nishiyama, Yutaka
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supporting information; experimental part
p. 1916 - 1919
(2011/05/14)
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- Horner-Wadsworth-Emmons modification for Ramirez gem-dibromoolefination of aldehydes and ketones using P(Oi-Pr)3
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A simple procedure for the use of triisopropylphosphite in the Ramirez olefination is described. This reagent is equally or more reactive than PPh 3 toward aldehydes and ketones in the gem-dibromoolefination of aldehydes and ketones. Under the
- Fang, Yuan-Qing,Lifchits, Olga,Lautens, Mark
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p. 413 - 417
(2008/04/01)
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- Olefination of aromatic ketones: Synthesis of mono- and dihaloalkenes
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A new simple and efficient transformation of various aromatic ketones to the corresponding halo (dihalo) alkenes is described. The reaction proceeds under mild conditions to give the target products in good yields.
- Korotchenko, Vasily N.,Shastin, Alexey V.,Nenajdenko, Valentine G.,Balenkova, Elisabeth S.
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p. 883 - 887
(2007/10/03)
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- A NEW AND CONVENIENT SYNTHESIS OF ARYL-SUBSTITUTED BUTATRIENES USING NICKEL-CATALYZED COUPLING OF ARYL-SUBSTITUTED 1,1-DIBROMOETHENES
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The reactions of aryl-substituted 1,1-dibromoethenes with in situ generated tetrakis(triphenylphosphine)nickel(0) in the presence of tetraethylammonium iodide give aryl-substituted butatrienes.
- Iyoda, Masahiko,Sakaitani, Masahiro,Miyazaki, Tatsuya,Oda, Masaji
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p. 2005 - 2006
(2007/10/02)
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