Arylethyne Bromoboration-Negishi Coupling Route to E- or Z-Aryl-Substituted Trisubstituted Alkenes of >= 98% Isomeric Purity. New Horizon in the Highly Selective Synthesis of Trisubstituted Alkenes

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F10%3A00023743" target="_blank" >RIV/60461373:22310/10:00023743 - isvavai.cz</a>

Výsledek na webu

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DOI - Digital Object Identifier

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Jazyk výsledku

angličtina

Název v původním jazyce

Arylethyne Bromoboration-Negishi Coupling Route to E- or Z-Aryl-Substituted Trisubstituted Alkenes of >= 98% Isomeric Purity. New Horizon in the Highly Selective Synthesis of Trisubstituted Alkenes

Popis výsledku v původním jazyce

The hitherto unprecedented palladium-catalyzed cross-coupling of (Z)-beta-bromo-beta-arylethenylboranes can be made to proceed satisfactorily through (1) the use of highly catalytically active bis(tri-tert-butylphosphine)palladium or dichloro[N,N-bis-(2,6-diisopropylphenyl)imidazol-2-yl](m-chloropyridine)palladium and (2) conversion of the dibromoboryl group to the (pinacol)boryl group. Thus, a wide variety of carbon groups can be used to substitute bromine in >= 98% stereo- and regioselectivity, whilesuppressing the otherwise dominant beta-debromoboration. Together with the alkylethyne-based protocols, the alkyne bromoboration Negishi coupling tandem process has emerged as the most widely applicable and highly selective route to trisubstituted alkenes including those that are otherwise difficult to access.

Název v anglickém jazyce

Arylethyne Bromoboration-Negishi Coupling Route to E- or Z-Aryl-Substituted Trisubstituted Alkenes of >= 98% Isomeric Purity. New Horizon in the Highly Selective Synthesis of Trisubstituted Alkenes

Popis výsledku anglicky

The hitherto unprecedented palladium-catalyzed cross-coupling of (Z)-beta-bromo-beta-arylethenylboranes can be made to proceed satisfactorily through (1) the use of highly catalytically active bis(tri-tert-butylphosphine)palladium or dichloro[N,N-bis-(2,6-diisopropylphenyl)imidazol-2-yl](m-chloropyridine)palladium and (2) conversion of the dibromoboryl group to the (pinacol)boryl group. Thus, a wide variety of carbon groups can be used to substitute bromine in >= 98% stereo- and regioselectivity, whilesuppressing the otherwise dominant beta-debromoboration. Together with the alkylethyne-based protocols, the alkyne bromoboration Negishi coupling tandem process has emerged as the most widely applicable and highly selective route to trisubstituted alkenes including those that are otherwise difficult to access.

Druh

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

CEP obor

CC - Organická chemie

OECD FORD obor

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Projekt

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Návaznosti

Z - Vyzkumny zamer (s odkazem do CEZ)

Rok uplatnění

2010

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

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Svazek periodika

352

Číslo periodika v rámci svazku

4

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

5

Strana od-do

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Kód UT WoS článku

000276052100006

EID výsledku v databázi Scopus

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