Ni-Catalyzed Carboxylation of Unactivated Primary Alkyl Bromides and Sulfonates with CO2
نویسندگان
چکیده
منابع مشابه
Palladium-catalyzed direct carboxylation of aryl bromides with carbon dioxide.
A novel protocol for the direct carbon dioxide insertion (CO(2)) into aryl halides in a catalytic manner is presented herein. Unlike other carboxylation methods using CO(2), there is no need for the synthesis of the corresponding organometallic intermediates. Additionally, and in contrast to the well-established carbonylation processes, our protocol does not use highly toxic CO for the preparat...
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Ni-catalyzed ketone formation through mild reductive coupling of a diverse set of unactivated alkyl bromides and iodides with particularly aryl acid anhydrides was successfully developed using zinc as the terminal reductant. These conditions also allow direct coupling of alkyl iodides with aryl acids in the presence of Boc(2)O and MgCl(2).
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In Ni(0)-catalyzed carboxylation reaction of aryl chloride with CO2, the formation of a Ni(I) species is crucial, because the CO2 insertion into the Ni(I)-Ph bond easily occurs but that into the Ni(II)-Ph bond cannot. This is a key point of this successful carboxylation reaction.
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A variety of arylboronic esters were efficiently carboxylated with CO(2) using a simple AgOAc/PPh(3) catalyst, affording the corresponding carboxylic acids in good yield. This simple and efficient silver(i) catalytic system showed wide functional group compatibility.
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The recent years have witnessed the development of metal-catalyzed reductive carboxylation of organic (pseudo)halides with CO2 as C1 source, representing potential powerful alternatives to existing methodologies for preparing carboxylic acids, privileged motifs in a myriad of pharmaceuticals and molecules displaying significant biological properties. While originally visualized as exotic cross-...
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ژورنال
عنوان ژورنال: Journal of the American Chemical Society
سال: 2014
ISSN: 0002-7863,1520-5126
DOI: 10.1021/ja5064586