- Generation of cycloalkynes through deprotonation of cyclic enol triflates with magnesium bisamides
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Deprotonative generation of cyclohexynes, cycloheptynes, and cyclooctynes was achieved by controlling the reactivities of transient anionic species from the corresponding enol triflates with magnesium bis(2,2,6,6-tetramethylpiperidide) as a base. The star
- Hioki, Yuto,Okano, Kentaro,Mori, Atsunori
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supporting information
p. 2614 - 2617
(2017/03/09)
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- Catalytic Multisite-Selective Acetoxylation Reactions at sp2 vs sp3 C-H Bonds in Cyclic Olefins
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The first Pd-catalyzed multisite-selective acetoxylation reactions are disclosed at an unactivated alkene sp2 C-H bond versus secondary allylic sp3 C-H bond in cyclic olefins via the modulation of directing groups. The different directing groups overcome the key challenge in differentiating C-H bonds and provide a new controlling approach for site-specific C-H activation. A wide variety of substrates are readily acetoxylated under operationally simple conditions. Mechanistic studies suggest that different Pd (IV) intermediates were involved in the multisite-selective acetoxylation reactions.
- Zang, Zhong-Lin,Zhao, Sheng,Karnakanti, Shuklachary,Liu, Cheng-Lin,Shao, Pan-Lin,He, Yun
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supporting information
p. 5014 - 5017
(2016/10/14)
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- Selective iron-catalyzed cross-coupling reactions of Grignard reagents with enol triflates, acid chlorides, and dichloroarenes
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Cheap, readily available, air stable, nontoxic, and environmentally benign iron salts such as Fe(acac)3 are excellent precatalysts for the cross-coupling of Grignard reagents with alkenyl triflates and acid chlorides. Moreover, it is shown that dichloroarene and -heteroarene derivatives as the substrates can be selectively monoalkylated by this method. All cross-coupling reactions proceed very rapidly under notably mild conditions and turned out to be compatible with a variety of functional groups in both reaction partners. A detailed analysis of the preparative results suggests that iron-catalyzed C-C bond formations can occur via different pathways. Thus, it is likely that reactions of methylmagnesium halides involve iron-ate complexes as the active components, whereas reactions of Grignard reagents with two or more carbon atoms are effected by highly reduced iron-clusters of the formal composition [Fe(MgX)2]n generated in situ. Control experiments using the ate-complex [Me4Fe]Li2 corroborate this interpretation.
- Scheiper, Bodo,Bonnekessel, Melanie,Krause, Helga,Fuerstner, Alois
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p. 3943 - 3949
(2007/10/03)
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- New electrochemical carboxylation of vinyl triflates. Synthesis of β-keto carboxylic acids
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Electrochemical reduction of alicyclic vinyl triflates (1a-1e) in a DMF solution containing 0.1 M Bu4NBF4 under an atmospheric pressure of carbon dioxide with a platinum cathode and a magnesium anode resulted in the cleavage of an ox
- Kamekawa, Hisato,Senboku, Hisanori,Tokuda, Masao
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p. 1591 - 1594
(2007/10/03)
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- The Conversion of Vinyl Triflates into γ'-Hydroxy-α,β-enones
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Vinyl triflates have been converted into γ'-hydroxy-α,β-enones through their palladium-catalysed coupling with 1-butyn-4-ols followed by the reaction of the obtained 1-hydroxy-3-yn-5-enes in an acidic CH2Cl2/3N HCl two-phase system in the presence of n-Bu
- Arcadi, Antonio,Cacchi, Sandro,Marinelli, Fabio
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p. 4955 - 4964
(2007/10/02)
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- A METHOD FOR THE REGIOSPECIFIC SYNTHESIS OF ENOL TRIFLATES BY ENOLATE TRAPPING
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Enol triflates can be prepared in high yield from regiospecifically generated enolates by trapping with N-phenyltrifluoromethanesulfonimide.
- Mc Murray, John E.,Scott, William J.
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p. 979 - 982
(2007/10/02)
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