Catalytic efficiency of a new tridentate ferrocenyl phosphine auxiliary: Sonogashira cross-coupling reactions of alkynes with aryl bromides and chlorides at low catalyst loadings of 10(-1) to 10(-4) mol

Catalytic efficiency of a new tridentate ferrocenyl phosphine auxiliary: Sonogashira cross-coupling reactions of alkynes with aryl bromides and chlorides at low catalyst loadings of 10(-1) to 10(-4) mol

[structure: see text] The catalytic activity in Sonogashira cross-coupling reactions of alkynes with a variety of aryl halides (including chlorides) using a multidentate ferrocenyl phosphine is presented. The novel mixed ferrocenyl aryl/alkyl triphosphine is thermally stable and insensitive to air o...

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Veröffentlicht in:Organic letters 2004-09, Vol.6 (20), p.3473-3476
Hauptverfasser: Hierso, Jean-Cyrille, Fihri, Aziz, Amardeil, Régine, Meunier, Philippe, Doucet, Henri, Santelli, Maurice, Ivanov, Vladimir V
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container_end_page 3476
container_issue 20
container_start_page 3473
container_title Organic letters
container_volume 6
creator Hierso, Jean-Cyrille
Fihri, Aziz
Amardeil, Régine
Meunier, Philippe
Doucet, Henri
Santelli, Maurice
Ivanov, Vladimir V
description [structure: see text] The catalytic activity in Sonogashira cross-coupling reactions of alkynes with a variety of aryl halides (including chlorides) using a multidentate ferrocenyl phosphine is presented. The novel mixed ferrocenyl aryl/alkyl triphosphine is thermally stable and insensitive to air or moisture, and its robustness allows aryl alkynylation at 10(-1) to 10(-4) mol % catalyst loadings with TONs up to 250,000. Copper-free coupling using phenylacetylene is also accessible in good yield.
doi_str_mv 10.1021/ol048870z
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title Catalytic efficiency of a new tridentate ferrocenyl phosphine auxiliary: Sonogashira cross-coupling reactions of alkynes with aryl bromides and chlorides at low catalyst loadings of 10(-1) to 10(-4) mol
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