scholarly journals Cobalt-catalyzed peri-selective alkoxylation of 1-naphthylamine derivatives

2018 ◽  
Vol 14 ◽  
pp. 2090-2097 ◽  
Author(s):  
Jiao-Na Han ◽  
Cong Du ◽  
Xinju Zhu ◽  
Zheng-Long Wang ◽  
Yue Zhu ◽  
...  
Keyword(s):  
Catalytic System ◽  
Functional Group ◽  
Secondary Alcohols ◽  
Reaction Conditions ◽  
Biologically Relevant ◽  
Efficient Approach ◽  
Directing Group ◽  
Aryl Ethers

A cobalt-catalyzed C(sp2)–H alkoxylation of 1-naphthylamine derivatives has been disclosed, which represents an efficient approach to synthesize aryl ethers with broad functional group tolerance. It is noteworthy that secondary alcohols, such as hexafluoroisopropanol, isopropanol, isobutanol, and isopentanol, were well tolerated under the current catalytic system. Moreover, a series of biologically relevant fluorine-aryl ethers were easily obtained under mild reaction conditions after the removal of the directing group.

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.

scholarly journals Sodium Copper Chlorophyllin Catalyzed Chemoselective Oxidation of Benzylic Alcohols and Diarylmethanes in Water

Molecules ◽  
2018 ◽  
Vol 23 (8) ◽  
pp. 1883 ◽  
Author(s):  
Shi-juan Liu ◽  
Miao Zhang ◽  
Rong Lu ◽  
Xiu-ying Li ◽  
Guang-bo Che
Keyword(s):  
Catalytic System ◽  
Functional Group ◽  
Secondary Alcohols ◽  
Benzylic Alcohols ◽  
Highly Efficient ◽  
Aryl Ketones ◽  
Sodium Copper Chlorophyllin

We report the highly efficient and chemoselective oxidation of benzylic alcohols catalyzed by sodium copper chlorophyllin in water, producing corresponding arylcarbonyl compounds. Importantly, the catalytic system exhibits a wide substrate scope and high functional group tolerance. Moreover, secondary alcohols and even diarylmethanes were smoothly oxidized to the desired aryl ketones with excellent yields.

Differentiation and Functionalization of Adjacent, Remote C–H Bonds

2019 ◽  
Author(s):  
Hang Shi ◽  
Lu Yi ◽  
Jiang Weng ◽  
Katherine Bay ◽  
Xiangyang Chen ◽  
...  
Keyword(s):  
Catalytic System ◽  
Functional Group ◽  
Hydrocinnamic Acid ◽  
Molecular Architectures ◽  
Site Selective ◽  
Developing Strategies

<p>Site-selective functionalizations of C–H bonds will ultimately afford chemists transformative tools for editing and constructing complex molecular architectures<sup>1-4</sup>. Towards this goal, developing strategies to activate C–H bonds that are distal from a functional group is essential<sup>4-6</sup>. In this context, distinguishing remote C–H bonds on adjacent carbon atoms is an extraordinary challenge due to the lack of electronic or steric bias between the two positions. Herein, we report the design of a catalytic system leveraging a remote directing template and a transient norbornene mediator to selectively activate a previously inaccessible remote C–H bond that is one bond further away. The generality of this approach has been demonstrated with a range of heterocycles, including a complex anti-leukemia agent, and hydrocinnamic acid substrates.</p>

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.

Modern Organic Synthesis in the Laboratory

2008 ◽  
Author(s):  
Jie Jack Li ◽  
Chris Limberakis ◽  
Derek A. Pflum
Keyword(s):  
Organic Chemistry ◽  
Graduate Students ◽  
Organic Synthesis ◽  
Functional Group ◽  
Bond Formation ◽  
Reaction Conditions ◽  
Carbon Bond ◽  
Oxidation Reduction ◽  
Carbon Carbon Bond ◽  
Daunting Task

Searching for reaction in organic synthesis has been made much easier in the current age of computer databases. However, the dilemma now is which procedure one selects among the ocean of choices. Especially for novices in the laboratory, it becomes a daunting task to decide what reaction conditions to experiment with first in order to have the best chance of success. This collection intends to serve as an "older and wiser lab-mate" one could have by compiling many of the most commonly used experimental procedures in organic synthesis. With chapters that cover such topics as functional group manipulations, oxidation, reduction, and carbon-carbon bond formation, Modern Organic Synthesis in the Laboratory will be useful for both graduate students and professors in organic chemistry and medicinal chemists in the pharmaceutical and agrochemical industries.

Nickel-Catalyzed Multicomponent Coupling Reaction of Alkyl Halides, Isocyanides and H2O: An Expedient Way to Access Alkyl Amides

Synthesis ◽  
2020 ◽  
Vol 52 (22) ◽  
pp. 3466-3472
Author(s):  
Yunkui Liu ◽  
Bingwei Zhou ◽  
Qiao Li ◽  
Hongwei Jin
Keyword(s):  
Functional Group ◽  
Coupling Reaction ◽  
Alkyl Halides ◽  
Previous Literature ◽  
Catalytic Cycle ◽  
Reaction Conditions ◽  
Multicomponent Coupling ◽  
Easy Operation

We herein describe a Ni-catalyzed multicomponent coupling reaction of alkyl halides, isocyanides, and H2O to access alkyl amides. Bench-stable NiCl2(dppp) is competent to initiate this transformation under mild reaction conditions, thus allowing easy operation and adding practical value. Substrate scope studies revealed a broad functional group tolerance and generality of primary and secondary alkyl halides in this protocol. A plausible catalytic cycle via a SET process is proposed based on preliminary experiments and previous literature.

Rh(III)-Catalyzed Olefination and Alkylation of Arenes with Maleimides: A Tunable Strategy for C(sp2)–H Functionalization

Synthesis ◽  
2021 ◽  
Author(s):  
Hongji Li ◽  
Wenjie Zhang ◽  
Xueyan Liu ◽  
Zhenfeng Tian
Keyword(s):  
Room Temperature ◽  
Functional Group ◽  
Reaction Conditions ◽  
Bond Functionalization ◽  
Alkylation Process ◽  
Coupling Partner

AbstractWe herein report a new nitrogen-directed Rh(III)-catalyzed C(sp2)–H bond functionalization of N-nitrosoanilines and azoxybenzenes with maleimides as a coupling partner, in which the olefination/alkylation process can be finely controlled at room temperature by variation of the reaction conditions. This method shows excellent functional group tolerance, and presents a mild access to the resulting olefination/alkylation products in moderate to good yields.

Sulfonyl Radical Triggered Selective Iodosulfonylation and Bicycli-zations of 1,6-Dienes

2021 ◽  
Author(s):  
Shi-Ping Wu ◽  
Dong-Kai Wang ◽  
Qing-Qing Kang ◽  
Guo-Ping Ge ◽  
Hongxing Zheng ◽  
...  
Keyword(s):  
Functional Group ◽  
High Selectivity ◽  
Reaction Conditions ◽  
First Time

A novel sulfonyl radical triggered selective iodosulfonylation and bicyclizations of 1,6-dienes has been described for the first time. High selectivity and efficiency, mild reaction conditions, excellent functional group compatibility, and...

Ligand-Driven Advances in Iridium Catalyzed sp3 C-H Borylation: 2,2’-Dipyridylarylmethane

Synlett ◽  
2020 ◽  
Author(s):  
Margaret R Jones ◽  
Nathan D. Schley
Keyword(s):  
Recent Work ◽  
Organic Synthesis ◽  
Functional Group ◽  
Reaction Conditions ◽  
Recent Advances ◽  
Additional Ligand ◽  
Limited Application ◽  
Hydrocarbon Substrates ◽  
Phenanthroline Ligands

The field of catalytic C-H borylation has grown considerably since its founding, providing a means for the preparation of synthetically versatile organoborane products. While sp2 C-H borylation methods have found widespread and practical use in organic synthesis, the analogous sp3 C-H borylation reaction remains challenging and has seen limited application. Existing catalysts are often hindered by incomplete consumption of the diboron reagent, poor functional group tolerance, harsh reaction conditions, and the need for excess or neat substrate. These challenges acutely affect C-H borylation chemistry of unactivated hydrocarbon substrates, which has lagged in comparison to methods for the C-H borylation of activated compounds. Herein we discuss recent advances in sp3 C-H borylation of undirected substrates in the context of two particular challenges: (1) utilization of the diboron reagent and (2) the need for excess or neat substrate. Our recent work on the application of dipyridylarylmethane ligands in sp3 C-H borylation has allowed us to make contributions in this space and has presented an additional ligand scaffold to supplement traditional phenanthroline ligands.

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