- The Direct Conversion of α-Hydroxyketones to Alkynes
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Alkynes are highly important functional groups in organic chemistry, both as part of target structures and as versatile synthetic intermediates. In this study, a protocol for the direct conversion of α-hydroxyketones to alkynes is reported. In combination with the variety of synthetic methods that generate the required starting materials by forming the central C-C bond, it enables a highly versatile fragment coupling approach toward alkynes. A broad scope for this novel transformation is shown alongside mechanistic insights. Furthermore, the utility of our protocol is demonstrated through its application in concert with varied α-hydroxyketone syntheses, giving access to a broad spectrum of alkynes.
- Ghiringhelli, Francesca,Nattmann, Lukas,Bognar, Sabine,Van Gemmeren, Manuel
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p. 983 - 993
(2019/01/24)
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- Mechanism and scope of the cyanide-catalyzed cross silyl benzoin reaction
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In this work, cross silyl benzoin addition reactions between acylsilanes (1) and aldehydes (2) catalyzed by metal cyanides are described. Unsymmetrical aryl-, heteroaryl-, and alkyl-substituted benzoin adducts can be generated in moderate to excellent yie
- Linghu, Xin,Bausch, Cory C.,Johnson, Jeffrey S.
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p. 1833 - 1840
(2007/10/03)
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- Electrosynthesis of 1,2 diketones by reduction of aromatic esters at freshly metal coated electrodes: A novel coupling reaction
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The one-step electrosynthesis of 1,2 aryldiketones has been achieved by constant current electrolysis of aromatic esters in an undivided cell fitted with a cadmium coated cathode and a sacrificial magnesium anode. Evidence is given for a role of Mg2+ ions in the pathway of the reaction.
- Heintz, Monique,Devaud, Marguerite,Hebri, Hassan,Dunach, Elisabet,Troupel, Michel
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p. 2249 - 2252
(2007/10/02)
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- Trifluoromethanesulfonic (Triflic) Acid Catalyzed Transformations of α-Hydroxy Carbonyl Compounds
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Triflic acid catalyzed reaction of 2-hydroxy-2-adamantanecarboxylic acid results via ionizative decarbonylation in the formation of adamantanone.Under carbon monoxide pressure pinacol-type rearrangement gives 4,5-homoadamantanedione.Reactions of a series of α-hydroxy ketones result in fragmentation, deprotonation, and cyclization, respectively.The reactions and their suggested mechanism are discussed.
- Olah, George A.,Wu, An-hsiang
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p. 2531 - 2534
(2007/10/02)
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- ADDITION OF GRIGNARD REAGENTS TO O-TRIMETHYLSILYLATED CYANOHYDRINS: SYNTHESIS OF ACYLOINS
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Grignard reagents have been found to react readily with O-trimethylsilylated cyanohydrins to afford, after acid hydrolysis of intermediates, good yields of acyloins.
- Krepski, Larry R.,Heilmann, Steven M.,Rasmussen, Jerald K.
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p. 4075 - 4078
(2007/10/02)
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- α-HETEROSUBSTITUTED PHOSPHONATE CARBANIONS IX : DIETHYL 1-PHENYL-1-TRIMETHYLSILOXYMETHANE PHOSPHONATE AS AN ACYL ANION EQUIVALENT; A NOVEL METHOD FOR THE PREPARATION OF α-HYDROXYKETONES.
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Diethyl 1-phenyl-1-trimethylsiloxymethane phosphonate carbanion was found to react as an effective acyl anion equivalent in the preparation of α-hydroxy ketones from aliphatic and aromatic aldehydes and ketones.A 1,4-oxygen-oxygen silicon migration was also observed.
- Koenigkramer, Rusty E.,Zimmer, Hans
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p. 1017 - 1020
(2007/10/02)
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