- Cobalt-catalyzed cross-coupling of alkynyl Grignard reagents with alkenyl triflates
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Alkenyl triflates in combination with Co(acac)3 as a catalyst were found to be excellent coupling partners of alkynyl Grignard reagents, where no special additives (even a phosphine ligand) but a common solvent, THF, are required to obtain vari
- Shirakawa, Eiji,Sato, Takahiro,Imazaki, Yusuke,Kimura, Takahiro,Hayashi, Tamio
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Read Online
- Triple-Bond Insertion Triggers Highly Regioselective 1,4-Aminomethylamination of 1,3-Enynes with Aminals Enabled by Pd-Catalyzed C-N Bond Activation
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A highly chemo- and regioselective 1,4-aminomethylamination of simple enynes with aminals to allenic 1,5-diamines by taking advantage of C-N bond activation has been reported. The reaction proceeds under mild reaction conditions and can be performed under
- Zhang, Yanchen,Yu, Bangkui,Gao, Binjian,Zhang, Tianze,Huang, Hanmin
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supporting information
(2019/01/21)
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- Triple-Bond Insertion Triggers Highly Regioselective 1,4-Aminomethylamination of 1,3-Enynes with Aminals Enabled by Pd-Catalyzed C-N Bond Activation
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A highly chemo- and regioselective 1,4-aminomethylamination of simple enynes with aminals to allenic 1,5-diamines by taking advantage of C-N bond activation has been reported. The reaction proceeds under mild reaction conditions and can be performed under
- Zhang, Yanchen,Yu, Bangkui,Gao, Binjian,Zhang, Tianze,Huang, Hanmin
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supporting information
p. 535 - 539
(2019/01/24)
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- Silaborations of 1,3-enynes - Substrate controlled allene/1,3-diene selectivity
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(Chemical Equation Presented) Silaboration of 1,3-enynes catalyzed by group 10 metal complexes affords 1,3-dienes with vinylborane and vinylsilane functions or 1,2-dienes with allylborane and vinylsilane functions. The type of product formed is determined
- Lueken, Christian,Moberg, Christina
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supporting information; experimental part
p. 2505 - 2508
(2009/05/26)
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- Insertion of 1-chloro-1-lithioalkenes into organozirconocenes. A versatile synthesis of stereodefined unsaturated systems
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Hydrozirconation of alkenes and alkynes, followed by insertion of 1- halo-1-lithio-1-alkenes, generated in situ by lithium tetramethylpiperidide deprotonation of vinyl halides, affords vinylzirconocene species which may be further elaborated. The method provides easy access to many structures including terminal (3E)- and (3Z)-1,3-dienes and (3E,5E)- and (3Z,5E)-1,3,5- trienes, and internal (E,Z)-dienes,(E,Z,E)-trienes, and (1E, 3Z)1,3-dien-5- ynes. Insertion of 2-monosubstituted 1-halo-1-lithio-1-alkenes occurs with clean inversion of configuration of the sp2-carbenoid carbon. Carbenoids derived by deprotonation of 2,2-disubstituted 1-halo-1-alkenes gave poor stereocontrol probably due to isomerization before insertion into the organozirconium species. Insertion of vinyl carbenoids into alkynylzirconocenes affords terminal (3E)- or (3Z)-1,3-dien-5-ynes, internal (1E,3Z)-1,3-dien-5-ynes, and (Z)-3-en-1,5-diynes.
- Kasatkin, Aleksandr,Whitby, Richard J.
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p. 7039 - 7049
(2007/10/03)
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- Control of the Propargylic Radical Stabilization by Carbon-Chain Length in Manganese(III)-Mediated Reactions of 1-Alken-3-ynes. - A Facile Synthetic Way to Long-Chain 4-Acetoxy-5-alkynoic Acids
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By investigation of reactions of 1-alken-3-ynes RCC-CH=CH2 4 with acetic acid/ acetic anhydride, mediated by manganese(III) acetate, it has been found that the stabilization of propargylic radical adducts depends on the carbon-chain length of R in 4.R=C8H17 is shown to be the "critical" chain length when ligand transfer reaction appears to be the only way of stabilization of intermediates, thus providing a facile one-step access to long-chain 4-acetoxy-5-alkynoic caids.The dependence of the product ratios on the AcOH/Ac2O ratio has also been demonstrated. Key Words: 1-Alken-3-ynes / Manganese(III) acetate / Propargyl radical / Ligand-transfer reaction / Electron-transfer reaction
- Melikyan, Gagik G.,Mkrtchyan, Varsik M.,Badanyan, Shaliko O.,Vostrowsky, Otto,Bestmann, Hans Juergen
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p. 2037 - 2040
(2007/10/02)
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