New Phosphine Ligand Architectures Lead to Efficient Gold Catalysts for Cycloisomerization Reactions at Very Low Loading

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F18%3A00498623" target="_blank" >RIV/61388963:_____/18:00498623 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/00216208:11310/18:10383123

Výsledek na webu

<a href="http://dx.doi.org/10.1002/adsc.201800938" target="_blank" >http://dx.doi.org/10.1002/adsc.201800938</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1002/adsc.201800938" target="_blank" >10.1002/adsc.201800938</a>

Jazyk výsledku

angličtina

Název v původním jazyce

New Phosphine Ligand Architectures Lead to Efficient Gold Catalysts for Cycloisomerization Reactions at Very Low Loading

Popis výsledku v původním jazyce

A simple and efficient access to a new P-chiral, but so far racemic ligand class featuring ortho-trityl and ortho-biaryl motifs is reported. The phosphines are prepared by efficient three- to four-step modular syntheses from simple branched alkyl(diphenyl)phosphine oxides in 52-63% overall yield. They form stable gold complexes, which were characterized by X-ray crystallography and spectroscopic methods. Fundamental catalytic properties of the complexes were studied in 1,6-enyne cycloisomerization reactions of achiral substrates to benchmark their activity against the efficient achiral catalyst (JohnPhos)AuCl. The results show that the new complexes can be applied in amounts down to 100 ppm allowing the cycloisomerization reactions to be performed with turnover frequencies of 20000 h(-1) and turnover numbers of up to 10000 h(-1).

Název v anglickém jazyce

New Phosphine Ligand Architectures Lead to Efficient Gold Catalysts for Cycloisomerization Reactions at Very Low Loading

Popis výsledku anglicky

A simple and efficient access to a new P-chiral, but so far racemic ligand class featuring ortho-trityl and ortho-biaryl motifs is reported. The phosphines are prepared by efficient three- to four-step modular syntheses from simple branched alkyl(diphenyl)phosphine oxides in 52-63% overall yield. They form stable gold complexes, which were characterized by X-ray crystallography and spectroscopic methods. Fundamental catalytic properties of the complexes were studied in 1,6-enyne cycloisomerization reactions of achiral substrates to benchmark their activity against the efficient achiral catalyst (JohnPhos)AuCl. The results show that the new complexes can be applied in amounts down to 100 ppm allowing the cycloisomerization reactions to be performed with turnover frequencies of 20000 h(-1) and turnover numbers of up to 10000 h(-1).

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

Výsledek vznikl pri realizaci vícero projektů. Více informací v záložce Projekty.

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2018

Kód důvěrnosti údajů

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

Název periodika

Advanced Synthesis & Catalysis

ISSN

1615-4150

e-ISSN

—

Svazek periodika

360

Číslo periodika v rámci svazku

21

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

10

Strana od-do

4215-4224

Kód UT WoS článku

000449688000027

EID výsledku v databázi Scopus

2-s2.0-85053889970