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.

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.

Recent Advances in Transition-Metal-Catalyzed C–H Addition to Nitriles

Synthesis ◽  
2021 ◽  
Author(s):  
Wei-Wei Liao ◽  
Shu-Qiang Cui
Keyword(s):  
Transition Metal ◽  
Organic Synthesis ◽  
Recent Progress ◽  
Building Blocks ◽  
Short Review ◽  
Synthetic Approach ◽  
Bond Forming ◽  
Palladium Catalyzed ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

AbstractTransition-metal-catalyzed C–H bond addition to nitriles has emerged as a powerful synthetic approach for the construction of C–C bonds in organic synthesis. Due to the merits of atom- and step-economy, as well the easy availability of the starting materials, these transformations not only deliver acyclic aryl ketone products with nitriles­ as C-building blocks, but can also be utilized for the highly efficient­ assembly of azaheterocyclic skeletons using nitriles as C–N building blocks. This short review summarizes recent progress on transition-metal-catalyzed C–C bond-forming reactions based on C(sp2)–H and C(sp3)–H additions to nitriles.1 Introduction2 Palladium-Catalyzed C–H Addition to Nitriles2.1 Palladium-Catalyzed C–H Addition to Nitriles for the Preparation of Ketone (Imine) Products2.2 Palladium-Catalyzed C–H Addition to Nitriles for the Preparation of Azaheterocycles2.3 Palladium-Catalyzed C–H Addition to Nitriles/1,2-Rearangement3 Other Transition-Metal-Catalyzed C–H Additions to Nitriles4 Summary and Outlook

Enantioselective C–H Functionalization toward Silicon-Stereogenic Silanes

Synthesis ◽  
2022 ◽  
Author(s):  
Chuan He ◽  
Wei Yuan
Keyword(s):  
Transition Metal ◽  
Short Review ◽  
Synthetic Approach ◽  
Bond Functionalization ◽  
Recent Advances ◽  
Stereogenic Centers ◽  
Organosilicon Chemistry ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed ◽  
Shed Light

In recent years, transition-metal-catalyzed enantioselective C–H bond functionalization has emerged as a powerful and attractive synthetic approach to access silicon-stereogenic centers, which continues to give impetus for the innovation of chiral organosilicon chemistry. This short review is aimed to summarize recent advances in the construction of silicon-stereogenic silanes via transition-metal-catalyzed enantioselective C–H functionalization. We have endeavored to highlight the great potential of this methodology and hope that this review will shed light on new perspectives, inspire further research in this emerging area.

Early transition metal-catalyzed C–H alkylation: hydroaminoalkylation for Csp3–Csp3 bond formation in the synthesis of selectively substituted amines

2018 ◽  
Vol 54 (89) ◽  
pp. 12543-12560 ◽  
Author(s):  
P. M. Edwards ◽  
L. L. Schafer
Keyword(s):  
Transition Metal ◽  
Bond Formation ◽  
Protecting Group ◽  
Early Transition Metal ◽  
Directing Group ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed ◽  
Early Transition

Protecting group, directing group, and external oxidant free synthesis of structurally diverse amines.

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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