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• W2898818079 endingPage "14516" @default.
• W2898818079 startingPage "14503" @default.
• W2898818079 abstract "Despite the significant progress, C-H arylation with aryldiazonium salts is a major challenge because of the faster rate of oxidative addition compared to the C-H insertion, leading to a deleterious homocoupling product. Recently, this limitation has been overcome by merging a photoredox catalyst with transition-metal catalysts which proceeds through a distinct single electron-transfer mechanism. However, we have observed that the photoredox catalyst is not necessary for the C-H arylation of aniline rather chemical reactivity can be controlled by tuning the electronic nature of the substrate. We report, herein, a palladium-catalyzed C-H arylation of aniline carbamates with aryldiazonium salts under external oxidant, acid, base free conditions at room temperature. Mechanistic studies suggest that the present reaction proceeds through a directed electrophilic metalation pathway which is the slowest step. However, the oxidative addition may take place through either ionic (2e-) or radical (1e-) pathway to generate hypervalent Pd(IV) or Pd(III) intermediate, respectively. A facile reductive elimination from the hypervalent palladium complex furnishes the C-H arylation product under mild conditions. The carbamate directing group is easily removed from the product to obtain the corresponding ortho-arylated aniline, which is a precursor for plethora of carbazole alkaloids and other biologically active molecules. The reaction is scaled-up to gram scale to furnish the desired product in comparable yields. Finally, we have applied this C-H arylation methodology for the synthesis of series of carbazole alkaloids such as clausine V, clauszoline K, O-methoxymahanine, and O-methylmurrayamine-D." @default.
• W2898818079 created "2018-11-09" @default.
• W2898818079 creator A5012463801 @default.
• W2898818079 creator A5015090394 @default.
• W2898818079 creator A5023300512 @default.
• W2898818079 date "2018-10-31" @default.
• W2898818079 modified "2023-10-18" @default.
• W2898818079 title "Palladium-Catalyzed Ortho C–H Arylation of Aniline Carbamates with Diazonium Salts under Mild Conditions: Expedient Synthesis of Carbazole Alkaloids" @default.
• W2898818079 cites W1669612115 @default.
• W2898818079 cites W1776111994 @default.
• W2898818079 cites W1834057360 @default.
• W2898818079 cites W1929392462 @default.
• W2898818079 cites W1981599881 @default.
• W2898818079 cites W1982500424 @default.
• W2898818079 cites W1987255792 @default.
• W2898818079 cites W1987675518 @default.
• W2898818079 cites W1988113026 @default.
• W2898818079 cites W1993739100 @default.
• W2898818079 cites W1997770703 @default.
• W2898818079 cites W2001940622 @default.
• W2898818079 cites W2002396136 @default.
• W2898818079 cites W2009870957 @default.
• W2898818079 cites W2010101793 @default.
• W2898818079 cites W2016978898 @default.
• W2898818079 cites W2024559491 @default.
• W2898818079 cites W2025265883 @default.
• W2898818079 cites W2029615149 @default.
• W2898818079 cites W2037085799 @default.
• W2898818079 cites W2038999038 @default.
• W2898818079 cites W2048649500 @default.
• W2898818079 cites W2059575002 @default.
• W2898818079 cites W2061660584 @default.
• W2898818079 cites W2064775792 @default.
• W2898818079 cites W2064826779 @default.
• W2898818079 cites W2066309940 @default.
• W2898818079 cites W2071220182 @default.
• W2898818079 cites W2073101743 @default.
• W2898818079 cites W2076172311 @default.
• W2898818079 cites W2081910612 @default.
• W2898818079 cites W2088029106 @default.
• W2898818079 cites W2090490503 @default.
• W2898818079 cites W2090580648 @default.
• W2898818079 cites W2090863663 @default.
• W2898818079 cites W2091728422 @default.
• W2898818079 cites W2092174893 @default.
• W2898818079 cites W2092801479 @default.
• W2898818079 cites W2095007326 @default.
• W2898818079 cites W2100824055 @default.
• W2898818079 cites W2101297940 @default.
• W2898818079 cites W2103429015 @default.
• W2898818079 cites W2104187864 @default.
• W2898818079 cites W2105799165 @default.
• W2898818079 cites W2111696573 @default.
• W2898818079 cites W2116114820 @default.
• W2898818079 cites W2117902186 @default.
• W2898818079 cites W2134562655 @default.
• W2898818079 cites W2138631756 @default.
• W2898818079 cites W2141303780 @default.
• W2898818079 cites W2147567444 @default.
• W2898818079 cites W2151975187 @default.
• W2898818079 cites W2161881624 @default.
• W2898818079 cites W2162443149 @default.
• W2898818079 cites W2162882944 @default.
• W2898818079 cites W2163678503 @default.
• W2898818079 cites W2275216968 @default.
• W2898818079 cites W2287661492 @default.
• W2898818079 cites W2313224176 @default.
• W2898818079 cites W2314018283 @default.
• W2898818079 cites W2327558983 @default.
• W2898818079 cites W2330692875 @default.
• W2898818079 cites W2331312604 @default.
• W2898818079 cites W2331550511 @default.
• W2898818079 cites W2333883857 @default.
• W2898818079 cites W2399435542 @default.
• W2898818079 cites W2408152013 @default.
• W2898818079 cites W2431180280 @default.
• W2898818079 cites W2533421376 @default.
• W2898818079 cites W2573885910 @default.
• W2898818079 cites W2597346779 @default.
• W2898818079 cites W2604237993 @default.
• W2898818079 cites W2607100833 @default.
• W2898818079 cites W2734324432 @default.
• W2898818079 cites W2734540261 @default.
• W2898818079 cites W2736176361 @default.
• W2898818079 cites W2750687951 @default.
• W2898818079 cites W2764021631 @default.
• W2898818079 cites W2788997459 @default.
• W2898818079 cites W2792477877 @default.
• W2898818079 cites W2806571158 @default.
• W2898818079 cites W2949623356 @default.
• W2898818079 cites W2951186804 @default.
• W2898818079 cites W2951635282 @default.
• W2898818079 doi "https://doi.org/10.1021/acsomega.8b02009" @default.
• W2898818079 hasPubMedCentralId "https://www.ncbi.nlm.nih.gov/pmc/articles/6644385" @default.
• W2898818079 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/31458136" @default.
• W2898818079 hasPublicationYear "2018" @default.
• W2898818079 type Work @default.
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