Transition metals in organic synthesis highlights for the year 1994

Hegedus, Louis S.

doi:10.1016/0010-8545(95)00000-3

Cited by 22 publications

(2 citation statements)

References 835 publications

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“…Palladium-catalyzed carbon−carbon bond forming reactions of allylic esters have been widely used in organic synthesis. − Particularly notable has been the development of couplings of stabilized nucleophiles such as malonate. Carbon−carbon bond couplings of more basic nucleophiles have proven to be problematic.…”

Section: Introductionmentioning

confidence: 99%

Palladium-Catalyzed Arylation of Allylic Benzoates Using Hypervalent Siloxane Derivatives

Correia

DeShong

2001

J. Org. Chem.

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Section: Introductionmentioning

confidence: 99%

Palladium-Catalyzed Arylation of Allylic Benzoates Using Hypervalent Siloxane Derivatives

Correia

DeShong

2001

J. Org. Chem.

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“…Palladium-catalyzed allylic substitution is an efficient and highly stereoselective method for formation of carbon−carbon bonds, and the alkylation with stabilized carbon nucleophiles has been widely applied in organic synthesis. − The major characteristic of alkylation using stabilized nucleophiles is that it proceeds with retention of configuration at the least hindered site of the intermediate π-allyl complex …”

Section: Introductionmentioning

confidence: 99%

Regioselectivity in the Palladium-Catalyzed Addition of Carbon Nucleophiles to Carbocyclic Derivatives

et al. 2001

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The regioselectivity of Pd-catalyzed malonate additions and arylations to cycloalkenyl esters can be predicted by completing a stereochemical analysis of the Pd-pi-allyl complex. The Pd-catalyzed malonate additions which have the greatest degree of regioselectivity are in which substituents have a steric influence in blocking the incoming nucleophile. Cyclopentenyl substrates displayed lower regioselectivity than the cyclohexyl counterparts presumably due to increased planarity of the system. Arylations using tin and hypervalent silicon reagents were compared.

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Transmetallierung von Tetraalkinylstannanen mit Grignard-Reagentien: eine Synthesemethode für Mono- und Dialkylzinnverbindungen

1999

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Monoalkyltrialkinyl‐ und Dialkyldialkinylstannane können selektiv durch Transmetallierung von Tetraalkinylstannanen mit Grignard‐Reagentien hergestellt werden; ein Beispiel ist in Gleichung (1) gegeben. Auf diese Weise sind Mono‐ oder Dialkylzinnverbindungen gut zugänglich, ohne daß starke Elektrophile eingesetzt werden müssen, denn die labile Sn‐C(Alkinyl)‐Bindung ermöglicht es, daß die Produkte leicht weiter umgesetzt werden können zu Alkylzinnoxiden, ‐chloriden und ‐alkoxiden.

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Transition metals in organic synthesis highlights for the year 1994

Cited by 22 publications

References 835 publications

Palladium-Catalyzed Arylation of Allylic Benzoates Using Hypervalent Siloxane Derivatives

Palladium-Catalyzed Arylation of Allylic Benzoates Using Hypervalent Siloxane Derivatives

Regioselectivity in the Palladium-Catalyzed Addition of Carbon Nucleophiles to Carbocyclic Derivatives

Transmetallierung von Tetraalkinylstannanen mit Grignard-Reagentien: eine Synthesemethode für Mono- und Dialkylzinnverbindungen

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