Copper-catalyzed coupling of aryl halides and nitrite salts: a mild Ullmann-type synthesis of aromatic nitro compounds

Saito, Shinichi; Koizumi, Yuichiro

doi:10.1016/j.tetlet.2005.05.033

Cited by 94 publications

(36 citation statements)

References 49 publications

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“…111 This was the first example of a cross-coupling route to these important compounds. The scope of this approach has recently been significantly extended by the use of a Pd-based catalyst.…”

Section: Copper-catalyzed Methodsmentioning

confidence: 95%

Diamine ligands in copper-catalyzed reactions

2010

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The utility of copper-mediated cross-coupling reactions has been significantly increased by the development of mild reaction conditions and the ability to employ catalytic amounts of copper. The use of diamine-based ligands has been important in these advances and in this review we discuss these systems, including the choice of reaction conditions and applications in the synthesis of pharmaceuticals, natural products and designed materials.

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Section: Copper-catalyzed Methodsmentioning

confidence: 95%

Diamine ligands in copper-catalyzed reactions

2010

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“…More recently, Prakash and Olah disclosed a method for the conversion of aryl boronic acids to aryl nitro compounds 5. This was followed by a report from Saito disclosing a copper catalyst for the transformation of aryl iodides to nitrobenzenes 6. These processes were important advances in this field and provided complimentary nitration protocols to known chemistry; however, the substrate scope of these reactions was limited and did not include heterocycles.…”

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confidence: 99%

Pd-Catalyzed Conversion of Aryl Chlorides, Triflates, and Nonaflates to Nitroaromatics

2009

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An efficient Pd-catalyst for the transformation of aryl chlorides, triflates and nonaflates to nitroaromatics has been developed. This reaction proceeds under weekly basic conditions and displays a broad scope and excellent functional group compatibility. Moreover, this method allows for the synthesis of aromatic nitro compounds that cannot be accessed efficiently via other nitration protocols. Mechanistic insight into the trasmetallation step of the catalytic process is also reported.

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“…Copper catalyzed ipso ‐nitration of haloarenes with KNO 2 was reported by Kantam in 2012 . Saito et al developed nitration of aromatic halides in the presence of catalytic amounts of Cu bronze with n Bu 4 NNO 2 in 2005 . Buchwald and co‐workers developed a general Pd catalyzed nitration of prefunctionalized aryl chlorides, triflates, and nonaflates with NaNO 2 as a simple nitro source .…”

Section: Introductionmentioning

confidence: 99%

Silver‐Catalyzed Chemo‐ and Regioselective Nitration of Anilides

Kianmehr

Nasab

2018

Eur J Org Chem

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A new and efficient Ag‐catalyzed method for the nitration of anilides by using sodium nitrite as a cheap and available NO2 source has been developed. This C–H functionalization reaction is ortho‐selective, achieves moderate to high yields and shows excellent functional group tolerance. Furthermore, it provides a novel approach to ortho‐nitrated anilides, which are very tricky to access with traditional methods.

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Copper-catalyzed coupling of aryl halides and nitrite salts: a mild Ullmann-type synthesis of aromatic nitro compounds

Cited by 94 publications

References 49 publications

Diamine ligands in copper-catalyzed reactions

Diamine ligands in copper-catalyzed reactions

Pd-Catalyzed Conversion of Aryl Chlorides, Triflates, and Nonaflates to Nitroaromatics

Silver‐Catalyzed Chemo‐ and Regioselective Nitration of Anilides

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