Catalyst-Controlled C–H Functionalization of Adamantanes using Selective H-Atom Transfer

2019 ◽  
Author(s):  
Hai-Bin Yang ◽  
Abigail Feceu ◽  
David Martin
Keyword(s):  
Functional Group ◽  
New Method ◽  
Alkylation Reaction ◽  
Atom Transfer ◽  
Broad Scope ◽  
Direct Functionalization ◽  
Photochemical Systems ◽  
Substrate Competition

<p>A new method for the direct functionalization of diamondoids has been developed using photoredox and H-atom transfer catalysis. This C–H alkylation reaction has excellent chemoselectivity for the strong 3º C–H bonds of adamantanes in polyfunctional molecules. In substrate competition reactions, a reversal in selectivity is observed for the new H-atom transfer catalyst reported here when compared to six known photochemical systems. Derivatization of a broad scope of diamondoids and adamantane-containing drugs highlights the versatility and functional group tolerance of this C–H functionalization strategy.</p>

Catalyst-Controlled C–H Functionalization of Adamantanes using Selective H-Atom Transfer

2019 ◽  
Author(s):  
Hai-Bin Yang ◽  
Abigail Feceu ◽  
David Martin
Keyword(s):  
Functional Group ◽  
New Method ◽  
Alkylation Reaction ◽  
Atom Transfer ◽  
Broad Scope ◽  
Direct Functionalization ◽  
Photochemical Systems ◽  
Substrate Competition

<p>A new method for the direct functionalization of diamondoids has been developed using photoredox and H-atom transfer catalysis. This C–H alkylation reaction has excellent chemoselectivity for the strong 3º C–H bonds of adamantanes in polyfunctional molecules. In substrate competition reactions, a reversal in selectivity is observed for the new H-atom transfer catalyst reported here when compared to six known photochemical systems. Derivatization of a broad scope of diamondoids and adamantane-containing drugs highlights the versatility and functional group tolerance of this C–H functionalization strategy.</p>

scholarly journals Catalyst-Controlled C–H Functionalization of Adamantanes using Selective H-Atom Transfer

2018 ◽  
Author(s):  
Hai-Bin Yang ◽  
Abigail Feceu ◽  
David Martin
Keyword(s):  
Functional Group ◽  
New Method ◽  
Alkylation Reaction ◽  
Atom Transfer ◽  
Broad Scope ◽  
Direct Functionalization ◽  
Photochemical Systems ◽  
Substrate Competition

<p>A new method for the direct functionalization of diamondoids has been developed using photoredox and H-atom transfer catalysis. This C–H alkylation reaction has excellent chemoselectivity for the strong 3º C–H bonds of adamantanes in polyfunctional molecules. In substrate competition reactions, a reversal in selectivity is observed for the new H-atom transfer catalyst reported here when compared to six known photochemical systems. Derivatization of a broad scope of diamondoids and adamantane-containing drugs highlights the versatility and functional group tolerance of this C–H functionalization strategy.</p>

Catalytic Synthesis of Cyclic Guanidines via Hydrogen Atom Transfer and Radical-Polar Crossover

2020 ◽  
Author(s):  
Shunya Ohuchi ◽  
Hiroki Koyama ◽  
Hiroki Shigehisa
Keyword(s):  
Hydrogen Atom ◽  
Functional Group ◽  
Hydrogen Atom Transfer ◽  
Catalytic Synthesis ◽  
Membered Ring ◽  
Biologically Active ◽  
Atom Transfer ◽  
Powerful Method ◽  
Protective Groups ◽  
The Common

A catalytic synthesis of cyclic guanidines, which are found in many biologically active compounds and natu-ral products, was developed, wherein transition-metal hydrogen atom transfer and radical-polar crossover were employed. This mild and functional-group tolerant process enabled the cyclization of alkenyl guanidines bearing common protective groups, such as Cbz and Boc. This powerful method not only provided the common 5- and 6-membered rings but also an unusual 7-membered ring. The derivatization of the products afforded various heterocycles. We also investigated the se-lective cyclization of mono-protected or hetero-protected (TFA and Boc) alkenyl guanidines and their further derivatiza-tions.

Enantioselective alpha-Arylation of Benzamides via Synergistic Nickel and Metallaphotoredox Catalysis

2019 ◽  
Author(s):  
John Montgomery ◽  
Alexander W. Rand
Keyword(s):  
Catalytic System ◽  
Functional Group ◽  
Enantiomeric Excess ◽  
New Method ◽  
Aryl Bromides

A new method to access alpha-arylated benzamides has been enabled by metallaphotoredox catalysis. This system allows for non-directed C–H functionalization of N-alkyl benzamides using a dual nickel/iridium catalytic system to form tertiary stereocenters in good enantiomeric excess and moderate yields. This reaction shows excellent functional group compatibility and can be performed using a number of sterically and electronically different aryl bromides and secondary benzamides.

Enantioselective alpha-Arylation of Benzamides via Synergistic Nickel and Metallaphotoredox Catalysis

2019 ◽  
Author(s):  
John Montgomery ◽  
Alexander W. Rand
Keyword(s):  
Catalytic System ◽  
Functional Group ◽  
Enantiomeric Excess ◽  
New Method ◽  
Aryl Bromides

A new method to access alpha-arylated benzamides has been enabled by metallaphotoredox catalysis. This system allows for non-directed C–H functionalization of N-alkyl benzamides using a dual nickel/iridium catalytic system to form tertiary stereocenters in good enantiomeric excess and moderate yields. This reaction shows excellent functional group compatibility and can be performed using a number of sterically and electronically different aryl bromides and secondary benzamides.

Direct and metal-free oxidative amination of sp3 C–H bonds for the construction of 2-hetarylquinazolin-4(3H)-ones

2016 ◽  
Vol 3 (9) ◽  
pp. 1096-1099 ◽  
Author(s):  
Huanhuan Liu ◽  
Tianran Zhai ◽  
Shiteng Ding ◽  
Yalei Hou ◽  
Xiangyu Zhang ◽  
...  
Keyword(s):  
Transition Metal ◽  
Functional Group ◽  
New Method ◽  
Oxidative Amination ◽  
Metal Free ◽  
Mild Conditions

New method for synthesis of 2-hetarylquinazolin-4(3H)-ones from 2-aminobenzamides and (2-azaaryl)methanes under transition-metal free conditions, featuring a wide substrate scope with a broad range of functional group tolerance under mild conditions.

scholarly journals Photocatalytic Atom Transfer Radical Addition to Olefins Utilizing Novel Photocatalysts

Molecules ◽  
2019 ◽  
Vol 24 (9) ◽  
pp. 1644 ◽  
Author(s):  
Errika Voutyritsa ◽  
Ierasia Triandafillidi ◽  
Nikolaos V. Tzouras ◽  
Nikolaos F. Nikitas ◽  
Eleftherios K. Pefkianakis ◽  
...  
Keyword(s):  
Metal Complexes ◽  
Organic Synthesis ◽  
Alkyl Group ◽  
Radical Addition ◽  
Bidentate Ligand ◽  
Atom Transfer ◽  
Broad Scope ◽  
Atom Transfer Radical Addition ◽  
Terpyridine Ligands ◽  
Photocatalytic Reactions

Photocatalysis is a rapidly evolving area of research in modern organic synthesis. Among the traditional photocatalysts, metal-complexes based on ruthenium or iridium are the most common. Herein, we present the synthesis of two photoactive, ruthenium-based complexes bearing pyridine-quinoline or terpyridine ligands with extended aromatic conjugation. Our complexes were utilized in the atom transfer radical addition (ATRA) of haloalkanes to olefins, using bromoacetonitrile or bromotrichloromethane as the source of the alkyl group. The tailor-made ruthenium-based catalyst bearing the pyridine-quinoline bidentate ligand proved to be the best-performing photocatalyst, among a range of metal complexes and organocatalysts, efficiently catalyzing both reactions. These photocatalytic atom transfer protocols can be expanded into a broad scope of olefins. In both protocols, the photocatalytic reactions led to products in good to excellent isolated yields.

scholarly journals Copper-Catalyzed Amination of Vinyl Azides to α-Ketoamides

SynOpen ◽  
2019 ◽  
Vol 03 (04) ◽  
pp. 91-95
Author(s):  
Yu Wang ◽  
Dongling Zhang ◽  
Kaining Zhang ◽  
Zhenhua Liu ◽  
Jing Lin ◽  
...  
Keyword(s):  
Benzoic Acid ◽  
Catalytic System ◽  
Functional Group ◽  
Efficient Approach ◽  
Broad Scope ◽  
Vinyl Azides ◽  
Oxidative Generation

An efficient approach for the amination of vinyl azides with N,N-dialkylacylamides has been developed. By using this protocol, structurally important α-ketoamides can be easily synthesized. The key to success is not only the introduction of a Cu(I)/oxygen catalytic system but also the utilization of t-BuOCl and benzoic acid as additives. The reaction is operationally simple, scalable, and displays broad scope and functional group tolerance. A possible mechanism involving copper-catalyzed oxidative generation of peroxide radicals is proposed.

Fast construction of dianthraceno[a,e]pentalenes for OPV applications

2017 ◽  
Vol 4 (5) ◽  
pp. 711-716 ◽  
Author(s):  
Zhongbo Zhang ◽  
Haijun Fan ◽  
Xiaozhang Zhu
Keyword(s):  
Functional Group ◽  
New Method ◽  
Tandem Reaction ◽  
Palladium Catalyzed

A new method based on a palladium-catalyzed tandem reaction for the fast construction of a dianthraceno[a,e]pentalene (DAP) framework is developed, which gave a series of dianthraceno[a,e]pentalenes with good functional group tolerance, and it should be highlighted that five C–C bonds were formed in one reaction.

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