New Chemoselective Metalating Agents for Solid-Phase Synthesis

Kondo, Yoshinori; Komine, Takashi; Fujinami, Michihiko; Uchiyama, and Masanobu; Sakamoto, Takao

doi:10.1021/cc980021d

Cited by 40 publications

(22 citation statements)

References 41 publications

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“…[44,51] This reaction constitutes one of the most general and convenient preparation methods for an organometallic species [52] on the solid phase (Scheme 16) and is ideally suited for applications in combinatorial chemistry. Remarkably, the ester linker is not attacked under these reaction conditions (À 35 8C, 0.5 ± 1.0 h).…”

Section: Organometallic Chemistrymentioning

confidence: 99%

New Applications of Polyfunctional Organometallic Compounds in Organic Synthesis

Boudier

Bromm

Lotz

et al. 2000

Angew. Chem. Int. Ed.

315

115

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In the second half of the twentieth century much effort was invested in the preparation of highly reactive polar organometallic reagents. The high reactivity of these reagents precluded the presence of many functional groups and often good chemoselectivities and stereoselectivities could only by achieved by transmetalation reactions. The synthesis of increasingly complex target molecules and the desire to avoid tedious protection–deprotection steps has led inevitably to the use of functionalized organometallic reagents in retrosynthesis. In the last fifteen years, the generation of organic derivatives of numerous metals and metalloids (Li, Mg, B, Zn, Sn) was investigated. In this review the most important preparations and applications of organometallic reagents in organic synthesis will be covered, with particular emphasis on organozinc reagents.

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Section: Organometallic Chemistrymentioning

confidence: 99%

New Applications of Polyfunctional Organometallic Compounds in Organic Synthesis

Boudier

Bromm

Lotz

et al. 2000

Angew. Chem. Int. Ed.

315

115

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“…[46] Bei funktionalisierten Iodimidazolen wie 54 lässt sich der Austausch bei À 40 8C durchführen. [44,51] Diese Reaktion ist somit eine der generellsten und bequemsten Methoden zur Herstellung einer festphasengebundenen Organometallverbindung [52] und daher ideal zur Anwendung in der kombinatorischen Chemie geeignet (Schema 16). [46] Während beim 4,5-Diiodimidazol 57 der Iod-Magnesium-Austausch aufgrund von Chelatstabilisierung bevorzugt an der 5-Position erfolgt, kann auch der kontrathermodynamische Austausch an der 4-Position vorgenommen werden, indem man den 5-Iodsubstituenten durch Brom ersetzt (Schema 12).…”

Section: Polyfunktionalisierte Organomagnesiumverbindungenunclassified

Neue Anwendungen für polyfunktionalisierte Organometallverbindungen in der organischen Synthese

et al. 2000

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In der zweiten Hälfte dieses Jahrhunderts wurde viel Forschungsarbeit in die Herstellung polarer Organometallreagentien investiert. Die hohe Reaktivität dieser Reagentien schloss die Gegenwart funktioneller Gruppen aus, und gute Chemo‐ und Stereoselektivitäten waren oft nur durch Transmetallierung zu erreichen. Die Synthese immer komplexerer Zielverbindungen und der Wunsch, ohne umständliche Schutzgruppenstrategien auszukommen, führten dazu, funktionalisierte Organometallreagentien in Retroynthesen zu verwenden. In den letzten 15 Jahren wurde die Herstellung organischer Derivate zahlreicher Metalle und Halbmetalle wie Li, Mg, B, Zn und Sn untersucht. Dieser Aufsatz fasst die wichtigsten Herstellungsmethoden und Anwendungen metallorganischer Reagentien in der organischen Synthese zusammen, wobei der Schwerpunkt auf Organozinkverbindungen liegt.

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“…Also, tBu 3 ZnLi (18) reacts readily with an electron-rich aryl iodide 32,p roviding the zincate 33,w hich leads to 34 after quenching with benzal-dehydein8 3% yield (Scheme 4). [11] Also, protected indoles( 35-36)a re suitable for such an exchange (Scheme 5). [12] Interestingly,t he yield is increased by 10 %b ya dding one equivalent of TMEDA (tetramethylethylenediamine) to Me 3 ZnLi (27).…”

Section: Introductionmentioning

confidence: 99%

Recent Advances of the Halogen–Zinc Exchange Reaction

Balkenhohl

Knöchel

2020

Chemistry A European J

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For the preparation of zinc organometallics bearing highly sensitive functional groups such as ketones, aldehydes or nitro groups, especially mild halogen–zinc exchange reagents have proven to be of great potential. In this Minireview, the latest research in the area of the halogen–zinc exchange reaction is reported, with a special focus lying on novel dialkylzinc reagents complexed with lithium alkoxides. Additionally, the preparation and application of organofluorine zinc reagents and transition‐metal‐catalyzed halogen–zinc exchange reactions are reviewed.

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New Chemoselective Metalating Agents for Solid-Phase Synthesis

Cited by 40 publications

References 41 publications

New Applications of Polyfunctional Organometallic Compounds in Organic Synthesis

New Applications of Polyfunctional Organometallic Compounds in Organic Synthesis

Neue Anwendungen für polyfunktionalisierte Organometallverbindungen in der organischen Synthese

Recent Advances of the Halogen–Zinc Exchange Reaction

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