Boron fluoride promoted opening of epoxides by organocopper and cuprate reagents

Alexakis, Alexandre; Jachiet, D.; Normant, Jean F.

doi:10.1016/s0040-4020(01)88165-5

Cited by 108 publications

(39 citation statements)

References 44 publications

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“…The 1 H NMR spectrum of the product was identical with that in the literature. [24] 2,6-Dimethylcyclohexanol (mixture of isomers; Table 13 Methyl 2-hydroxycyclohexanecarboxylate (cis and trans mixture; H NMR spectrum of the product was identical with that in the literature. [22] Cyclohexane-1,3-diol (cis and trans mixture; Table 14, entry 3; Table 15 …”

Section: Arene Hydrogenation In Iproh (Tables 6-16)supporting

confidence: 55%

Efficient and Practical Arene Hydrogenation by Heterogeneous Catalysts under Mild Conditions

Maegawa

Akashi

Yaguchi

et al. 2009

Chemistry A European J

139

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An efficient and practical arene hydrogenation procedure based on the use of heterogeneous platinum group catalysts has been developed. Rh/C is the most effective catalyst for the hydrogenation of the aromatic ring, which can be conducted in iPrOH under neutral conditions and at ordinary to medium H(2) pressures (<10 atm). A variety of arenes such as alkylbenzenes, benzoic acids, pyridines, furans, are hydrogenated to the corresponding cyclohexyl and heterocyclic compounds in good to excellent yields. The use of Ru/C, less expensive than Rh/C, affords an effective and practical method for the hydrogenation of arenes including phenols. Both catalysts can be reused several times after simple filtration without any significant loss of catalytic activity.

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Section: Arene Hydrogenation In Iproh (Tables 6-16)supporting

confidence: 55%

Efficient and Practical Arene Hydrogenation by Heterogeneous Catalysts under Mild Conditions

Maegawa

Akashi

Yaguchi

et al. 2009

Chemistry A European J

139

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“…Metalation of 35 with nBuLi, followed by transmetalation of the intermediate aryllithium derivative with copper cyanide, and addition of 2-methyl-2-vinyloxirane 36, gave the desired allylic alcohol 37 in 67% yield, but with a disappointing 2.5:1 E/Z ratio. [18] To solve this problem selenium dioxide allylic oxidation was chosen as the key step to control the stereochemistry of the double bond. Thus, the aryllithium reagent derived from 35 was alkylated with prenyl bromide to yield 38 (91%).…”

Section: Scheme 1 Retrosynthetic Analysis Of Usneoidonesmentioning

confidence: 99%

Enantioselective Synthesis of the Originally Proposed Usneoidone Structure: Evidence for a Structural Revision

et al. 2004

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“…[76] On the other hand, BF 3´E t 2 O accelerates conjugate addition [35] and alkylation of epoxides. [77] In the allylation chemistry, zinc-, [49] titanium-, [54] and aluminum- [78] based organocopper reagents show much higher S N 2' selectivity than lithium organocuprate. The Lewis acidity of the countercation to the organocuprate is undoubtedly important, but the mechanistic role still needs further studies [Eq.…”

Section: Lewis Acid Effects Of the Countercationmentioning

confidence: 99%

Wherefore Art Thou Copper? Structures and Reaction Mechanisms of Organocuprate Clusters in Organic Chemistry

Nakamura

Mori

2000

Angew. Chem. Int. Ed.

272

186

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Organocopper reagents provide the most general synthetic tools in organic chemistry for nucleophilic delivery of hard carbanions to electrophilic carbon centers. A number of structural and mechanistic studies have been reported and have led to a wide variety of mechanistic proposals, some of which might even be contradictory to others. With the recent advent of physical and theoretical methodologies, the accumulated knowledge on organocopper chemistry is being put together into a few major mechanistic principles. This review will summarize first the general structural features of organocopper compounds and the previous mechanistic arguments, and then describe the most recent mechanistic pictures obtained through high‐level quantum mechanical calculations for three typical organocuprate reactions, carbocupration, conjugate addition, and SN2 alkylation. The unified view on the nucleophilic reactivities of metal organocuprate clusters thus obtained has indicated that organocuprate chemistry represents an intricate example of molecular recognition and supramolecular chemistry, which chemists have long exploited without knowing it. Reasoning about the uniqueness of the copper atom among neighboring metal elements in the periodic table will be presented.

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Boron fluoride promoted opening of epoxides by organocopper and cuprate reagents

Cited by 108 publications

References 44 publications

Efficient and Practical Arene Hydrogenation by Heterogeneous Catalysts under Mild Conditions

Efficient and Practical Arene Hydrogenation by Heterogeneous Catalysts under Mild Conditions

Enantioselective Synthesis of the Originally Proposed Usneoidone Structure: Evidence for a Structural Revision

Wherefore Art Thou Copper? Structures and Reaction Mechanisms of Organocuprate Clusters in Organic Chemistry

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