2021
DOI: 10.1039/d1gc02602j
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Pd-Catalysed Suzuki–Miyaura cross-coupling of aryl chlorides at low catalyst loadings in water for the synthesis of industrially important fungicides

Abstract: The Suzuki-Miyaura coupling reaction of electron-poor aryl chlorides in the synthesis of crop protection-relevant active ingredients in water is disclosed. Optimisation of the reaction conditions allowed to run the reaction...

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Cited by 32 publications
(20 citation statements)
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“…In the present work, we propose that the well-reported mechanism (Scheme 4) occurs for two mechanistically different catalytic transformation reactions, as follows: (i) SM C-C 54,65 and (ii) nitro hydrogenation. 66 The SM C-C reaction involves oxidative addition, transmetallation and reductive elimination, while in the case of the nitro hydrogenation reaction, we propose the universal hydride transfer via the heterolytic cleavage of H 2 .…”
Section: Mechanismmentioning
confidence: 78%
“…In the present work, we propose that the well-reported mechanism (Scheme 4) occurs for two mechanistically different catalytic transformation reactions, as follows: (i) SM C-C 54,65 and (ii) nitro hydrogenation. 66 The SM C-C reaction involves oxidative addition, transmetallation and reductive elimination, while in the case of the nitro hydrogenation reaction, we propose the universal hydride transfer via the heterolytic cleavage of H 2 .…”
Section: Mechanismmentioning
confidence: 78%
“…While most of these approaches allow operation at low catalyst loadings, under mild conditions, and even in green solvents, including water [ 14 , 15 ], they all suffer from the limits related to homogeneous catalysis, which can be summarized in the direct costs for catalysts’ synthesis, and the indirect ones for their efficient recovery and reuse, which is also a key issue for the environmental impact of the process.…”
Section: Introductionmentioning
confidence: 99%
“…Coupling of C−C bonds is one of the key reactions to promote the progress of organic chemistry [1–3] . In particular, most of C−C bonds construction containing a series of natural, unnatural products and advanced compounds come from Pd‐catalysed Suzuki‐Miyaura coupling reaction [4–6] . Conventionally, Suzuki‐Miyaura coupling reaction was catalyzed by homogeneous Pd‐based materials with organic ligands using toxic solvents and under inert gas atmosphere at high temperature [7,8] .…”
Section: Introductionmentioning
confidence: 99%
“…[1][2][3] In particular, most of CÀ C bonds construction containing a series of natural, unnatural products and advanced compounds come from Pd-catalysed Suzuki-Miyaura coupling reaction. [4][5][6] Conventionally, Suzuki-Miyaura coupling reaction was catalyzed by homogeneous Pdbased materials with organic ligands using toxic solvents and under inert gas atmosphere at high temperature. [7,8] Obviously, on the one hand, the above reaction process inevitably uses a large amount of toxic solvents that is harmful to the environment and requires continuous heating under inert gas, which consumes a lot of energy and is cumbersome to operate.…”
Section: Introductionmentioning
confidence: 99%