Regiocontrolled palladium-catalyzed and copper-mediated C–H bond functionalization of protectedl-histidine

2014 ◽  
Vol 12 (23) ◽  
pp. 3792-3796 ◽  
Author(s):  
Amit Mahindra ◽  
Rahul Jain
Keyword(s):  
Transition Metal ◽  
Aryl Halides ◽  
Bond Functionalization ◽  
Palladium Catalyzed ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed ◽  
Coupling Partner

Regiocontrolled transition-metal-catalyzed C–H bond arylation of protectedl-histidine with aryl halides as the coupling partner is reported.

scholarly journals Exploration of C–H and N–H-bond functionalization towards 1-(1,2-diarylindol-3-yl)tetrahydroisoquinolines

2014 ◽  
Vol 10 ◽  
pp. 2186-2199 ◽  
Author(s):  
Michael Ghobrial ◽  
Marko D Mihovilovic ◽  
Michael Schnürch
Keyword(s):  
Transition Metal ◽  
Synthetic Approach ◽  
Protecting Group ◽  
Copper Salts ◽  
Bond Functionalization ◽  
Palladium Catalyzed ◽  
Synthetic Routes ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

The synthesis of 1,2,3-trisubstituted indoles was investigated. More specifically, straightforward synthetic routes towards 1-(1,2-diarylindol-3-yl)-N-PG-THIQs (PG = protecting group, THIQ = tetrahydroisoquinoline) employing transition metal-catalyzed C–H and N–H-bond functionalization were explored. It was found that the synthesis of the target compounds is strongly dependent on the order of events. Hence, depending on the requirements of a synthetic problem the most suitable and promising pathway can be chosen. Additionally, a new synthetic approach towards 1,2-diarylindoles starting from 1-arylindole could be established in the course of our investigation by using a palladium-catalyzed protocol. Such 1,2-diarylindoles were successfully reacted with N-Boc-THIQ to furnish 1,2,3-trisubstituted indoles as target compounds. Furthermore, regioselective N-arylation of protected and unprotected 1-(indol-3-yl)-THIQs was successfully conducted using either simple iron or copper salts as catalysts.

scholarly journals Advances in the Synthesis of Fluorinated Scaffolds by Transition Metal-Catalyzed C–H Bond Activation

2020 ◽  
Vol 74 (11) ◽  
pp. 871-877
Author(s):  
Sara Mazeh ◽  
Maria Ivana Lapuh ◽  
Tatiana Besset
Keyword(s):  
Transition Metal ◽  
Fluorine Atom ◽  
Bond Activation ◽  
Value Added ◽  
Bond Functionalization ◽  
Present Account ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

Thanks to the unique features of the fluorine atom and the fluorinated groups, fluorine-containing molecules are essential. Therefore, the search for new fluorinated groups as well as straightforward and original methodologies for their installation is of prime importance. Especially, the combination of organofluorine chemistry with transition metal-catalyzed C–H bond functionalization reactions offered straightforward tools to access original fluorinated scaffolds. In this context, over the last years, our group focused on the development of original methodologies to synthesize fluorine-containing molecules with a special attention to emergent fluorinated groups. The present account highlights our recent contributions to the synthesis of highly value-added fluorine-containing compounds by transition metal-catalyzed C–H bond activation.

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