- Electrochemical-Induced Hydrogenation of Electron-Deficient Internal Olefins and Alkynes with CH3OH as Hydrogen Donor
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Efficient hydrogenation of electron-deficient internal olefins and alkynes access to saturate ketone with CH3OH as a single hydrogen donor under electrochemical conditions has been successfully developed. This hydrogenation strategy can be used to convert electron-deficient internal olefins and alkynes to saturate ketone under electrochemical conditions with exogenous-reductant and a metal catalyst. Mechanistic studies reveal that radical hydrogenation was involved in this transformation. Notably, various electron-deficient internal olefins and alkynes could be tolerated in such an electrochemical hydrogenation synthetic strategy and can be easily scaled up with good efficiency. (Figure presented.).
- Qin, Hongyun,Yang, Jianjing,Yan, Kelu,Xue, Yaxuan,Zhang, Meichen,Sun, Xuejun,Wen, Jiangwei,Wang, Hua
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supporting information
p. 2104 - 2109
(2021/03/15)
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- Transition-Metal-Free Quinoline Synthesis from Acetophenones and Anthranils via Sequential One-Carbon Homologation/Conjugate Addition/Annulation Cascade
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A transition-metal-free method for the construction of functionalized quinolines from readily available acetophenones and anthranils is reported. This one-pot reaction cascade involves in situ generation of α,β-unsaturated ketones from the acetophenone via one-carbon homologation by DMSO followed by the aza-Michael addition of anthranils and subsequent annulation. DMSO acted in this reaction not only as solvent but also as one carbon source, thus providing a highly atom-economical and environmentally benign approach for the synthesis of 3-substituted quinolines.
- Wakade, Sandip Balasaheb,Tiwari, Dipak Kumar,Ganesh, Pothapragada S. K. Prabhakar,Phanindrudu, Mandalaparthi,Likhar, Pravin R.,Tiwari, Dharmendra Kumar
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supporting information
p. 4948 - 4951
(2017/09/23)
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- Transition Metal-Free α-Csp3-H Methylenation of Ketones to Form C=C Bond Using Dimethyl Sulfoxide as Carbon Source
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A direct α-Csp3-H methylenation of arylketones to form C=C bond using dimethyl sulfoxide as one-carbon source is achieved under transition metal-free reaction condition. Various aryl ketone derivatives react readily with DMSO, producing the α,β-unsaturated carbonyl compounds in yields of 42 to 90%. This method features a transition metal-free reaction condition, wide substrate scope and using DMSO as novel one-carbon source to form C=C bond, thus providing an efficient and expeditious approach to an important class of α,β-unsaturated carbonyl compounds. Based on the preliminary experiments, a plausible mechanism of this transformation is disclosed.
- Liu, Yu-Feng,Ji, Peng-Yi,Xu, Jing-Wen,Hu, Yu-Qun,Liu, Qiang,Luo, Wei-Ping,Guo, Can-Cheng
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supporting information
p. 7159 - 7164
(2017/07/26)
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- Transition metal-free C(sp3)-H bond coupling among three methyl groups
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A coupling of multiple C(sp3)-H bonds of the methyl group in methyl ketones with dimethyl sulfoxide is developed. This coupling allows the direct C(sp3)-H bond coupling among three methyl groups and affords one C-C bond and one CC bond under transition metal-free conditions. The value-added cyclized 3-methylthiomethyl chroman-4-ones can be synthesized through this method. A plausible mechanism is proposed.
- Liu, Yufeng,Zhan, Xi,Ji, Pengyi,Xu, Jingwen,Liu, Qiang,Luo, Weiping,Chen, Tieqiao,Guo, Cancheng
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supporting information
p. 5346 - 5349
(2017/07/10)
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- New ketone homoenolate anion equivalents derived from (alkenyl)pentamethyl phosphoric triamides
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Lithiated ambident anions derived from (1-alkyl-2-propenyl)- or (1-phenyl-2-propenyl)-pentamethyl phosphoric triamides undergo regioselectively γ-reaction with various alkylating reagents and isobutyraldehyde. Further hydrolysis of adducts releases the ketone under acid conditions. Number of synthetic applications clearly show the ketone homoenolate behaviour of these new carbanions.
- Grison, Claude,Thomas, Antoine,Coutrot, Frédéric,Coutrot, Philippe
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p. 2101 - 2123
(2007/10/03)
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- Stepwise controlled reduction of α-oxoketene dithioacetals with Zn/ZnCl2-TMEDA in ethanol
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α-Oxoketene dithioacetals 1 are shown to undergo highly selective conjugate reduction with Zn/ZnCl2-TMEDA in refluxing ethanol under controlled reaction conditions to afford β-methylthiomethylene ketones 6, β-methylthioketones 7 and the completely desulphurized α-methylketones 8 in sequential manner.
- Yadav, K. Mallik,Suresh, Joghee R.,Patro, Balaram,Ila, Hiriyakkanavar,Junjappa, Hiriyakkanavar
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p. 4679 - 4686
(2007/10/03)
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- 3-Metallated Enamines VI. Use as β-Oxo Vinyl Anion Equivalents
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Two possibilities to produce a synthetic equivalent for the β-oxo vinyl anion starting from a saturated carbonyl compound are investigated.In the first method, a methylthio group is introduced into the 3-position of the corresponding enamine.Metallation, regioselective attack by an electrophile followed by hydrolysis and oxidative elimination of the methylthio group completes the sequence.In the second method, the trimethyl silyl group is introduced instead.After deprotonation and regioselective reaction with an electrophile, the silylated enamine is chlorinated with N-chloro-succinimid.Dechlorosilylation and simultaneous hydrolysis of the enamine are achieved by means of trifluoro acetic acid/ hydrochloric acid and sodium fluoride in ethanol.
- Sudheendranath, C. S.,Ahlbrecht, H.
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p. 973 - 979
(2007/10/02)
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