The syn/anti-Dichotomy in the Palladium-Catalyzed Addition of Nucleophiles to Alkenes

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F15%3A10295241" target="_blank" >RIV/00216208:11310/15:10295241 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/61388963:_____/15:00443145

Výsledek na webu

<a href="http://dx.doi.org/10.1002/chem.201404070" target="_blank" >http://dx.doi.org/10.1002/chem.201404070</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1002/chem.201404070" target="_blank" >10.1002/chem.201404070</a>

Jazyk výsledku

angličtina

Název v původním jazyce

The syn/anti-Dichotomy in the Palladium-Catalyzed Addition of Nucleophiles to Alkenes

Popis výsledku v původním jazyce

In this review the stereochemistry of palladium-catalyzed addition of nucleophiles to alkenes is discussed, and examples of these reactions in organic synthesis are given. Most of the reactions discussed involve oxygen and nitrogen nucleophiles; the Wacker oxidation of ethylene has been reviewed in detail. An anti-hydroxypalladation in the Wacker oxidation has strong support from both experimental and computational studies. From the reviewed material it is clear that anti-addition of oxygen and nitrogennucleophiles is strongly favored in intermolecular addition to olefin-palladium complexes even if the nucleophile is coordinated to the metal. On the other hand, syn-addition is common in the case of intramolecular oxy- and amidopalladation as a resultof the initial coordination of the internal nucleophile to the metal.

Název v anglickém jazyce

The syn/anti-Dichotomy in the Palladium-Catalyzed Addition of Nucleophiles to Alkenes

Popis výsledku anglicky

In this review the stereochemistry of palladium-catalyzed addition of nucleophiles to alkenes is discussed, and examples of these reactions in organic synthesis are given. Most of the reactions discussed involve oxygen and nitrogen nucleophiles; the Wacker oxidation of ethylene has been reviewed in detail. An anti-hydroxypalladation in the Wacker oxidation has strong support from both experimental and computational studies. From the reviewed material it is clear that anti-addition of oxygen and nitrogennucleophiles is strongly favored in intermolecular addition to olefin-palladium complexes even if the nucleophile is coordinated to the metal. On the other hand, syn-addition is common in the case of intramolecular oxy- and amidopalladation as a resultof the initial coordination of the internal nucleophile to the metal.

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CC - Organická chemie

OECD FORD obor

—

Projekt

—

Návaznosti

S - Specificky vyzkum na vysokych skolach<br>I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2015

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Chemistry - A European Journal

ISSN

0947-6539

e-ISSN

—

Svazek periodika

21

Číslo periodika v rámci svazku

1

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

21

Strana od-do

36-56

Kód UT WoS článku

000346735000001

EID výsledku v databázi Scopus

2-s2.0-84920587987