- Visible-Light-Mediated Ru-Catalyzed Synthesis of 3-(Arylsulfonyl)but-3-enals via Coupling of α-Allenols with Diazonium Salts and Sulfur Dioxide
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The first coupling of α-allenols, sulfur dioxide, and arenediazonium salts is presented. The three-component reaction which is promoted by visible light can be easily accomplished using DABSO as a sulfur dioxide surrogate in the presence of a photoredox catalyst. In this manner, a broad range of electron-rich and electron-deficient aryl substituents are well accommodated in the sulfonylation-rearrangement cascade to afford the 2,2-disubstituted 3-(arylsulfonyl)but-3-enals in reasonable yields. Based on control experiments, a radical mechanism which does imply 1,2-aryl migration has been proposed.
- Herrera, Fernando,Luna, Amparo,Almendros, Pedro
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supporting information
p. 9490 - 9494
(2020/12/21)
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- Lewis Acid-Mediated Cyclization of Allenyl Aryl Ketones
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The cyclization of a series of nonheterocyclic allenyl aryl ketones was examined using boron trifluoride etherate and indium triflate to mediate the reaction. Yields with BF3 were low in most instances due mainly to competitive destruction of t
- Zaky, Mariam,Li, Zhe,Morgan, Timothy D. R.,Lefort, Fran?ois M.,Boyd, Russell J.,Burnell, D. Jean
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p. 13665 - 13675
(2019/10/16)
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- Acid-catalyzed synthesis of α,β-disubstituted conjugated enones by a Meyer-Schuster-type rearrangement in allenols
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A novel, direct and simple methodology to gain access to α,β-disubstituted conjugated enones from α-allenols in a sustainable metal catalysis context, considering the inexpensiveness and environmentally friendliness of iron(III) species and protons, has b
- Alcaide, Benito,Almendros, Pedro,Cembellín, Sara,Martínez Del Campo, Teresa
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supporting information
p. 1070 - 1078
(2015/03/30)
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- Reaction of two different α-allenols in a heterocyclization/cross- coupling sequence: Convenient access to functionalized buta-1,3-dienyl dihydrofurans
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(Chemical Equation Presented) In a single step a highly functionalized buta-1,3-dienyl-substituted 2,5-dihydrofuran unit can be formed from two different α-allenol derivatives through a novel heterocyclization/cross- coupling sequence (see scheme). The re
- Alcaide, Benito,Almendros, Pedro,Martinez Del Campo, Teresa
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p. 4501 - 4504
(2007/10/03)
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- On pentaorganylstiborane. III. Regio- and diastereoselective additions of acetylenic and allenic organoantimony compounds to aldehydes
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The reaction of propargyl bromide (4a) with tributylstibine gave allenyltributylstibonium bromide (5), and its corresponding pentaorganylstiborane reacted with aldehyde to give homopropargylic alcohol (10a) exclusively in good yield.However, the reaction
- Zhang, Li-Jun,Mo, Xue-Sheng,Huang, Yao-Zeng
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- Selective Synthesis of Allenic and Acetylenic Derivatives via Pentaorganylstiboranes
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Allenyltetrabutylstiborane (3), formed from allenyltributylstibonium bromide (2) and butylmagnesium bromide, reacted with aldehydes to give homopropargylic alcohols (4) exclusively in excellent yields, while 2-butynyltetrabutylstiborane (6), formed from 2
- Zhang, Li-Jun,Huang, Yao-Zeng,Huang, Zhe-Hui
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p. 6579 - 6582
(2007/10/02)
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