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 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.

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.

Direct synthesis of indazole derivatives via Rh(iii)-catalyzed C–H activation of phthalazinones and allenes

2021 ◽  
Vol 19 (35) ◽  
pp. 7701-7705
Author(s):  
Chuanliu Yin ◽  
Tianshuo Zhong ◽  
Xiangyun Zheng ◽  
Lianghao Li ◽  
Jian Zhou ◽  
...  
Keyword(s):  
Catalytic System ◽  
Functional Group ◽  
Direct Synthesis ◽  
Atom Economy

An Rh(iii)-catalyzed annulation of phthalazinones and various allenes was developed, leading to the formation of indazole derivatives. This catalytic system exhibits excellent functional group tolerance and atom economy.

scholarly journals Gold(I)-catalyzed synthesis of γ-vinylbutyrolactones by intramolecular oxaallylic alkylation with alcohols

2011 ◽  
Vol 7 ◽  
pp. 1198-1204 ◽  
Author(s):  
Michel Chiarucci ◽  
Mirko Locritani ◽  
Gianpiero Cera ◽  
Marco Bandini
Keyword(s):  
Catalytic System ◽  
Functional Group ◽  
Direct Synthesis ◽  
Catalytic Process ◽  
Primary Alcohols

Gold(I)-N-heterocyclic carbene (NHC) complexes proved to be a reliable catalytic system for the direct synthesis of functionalized γ-vinylbutyrolactones by intramolecular oxaallylic alkylation with primary alcohols. Good isolated chemical yields were obtained for a range of malonyl and acetate derivatives. The good performance in reagent-grade solvents and the functional group/moisture tolerance make this catalytic process a promising route for the synthesis of architecturally complex polycyclic structures.

CuSO4–d-glucose, an inexpensive and eco-efficient catalytic system: direct access to diverse quinolines through modified Friedländer approach involving SNAr/reduction/annulation cascade in one pot

RSC Advances ◽  
2015 ◽  
Vol 5 (10) ◽  
pp. 7654-7660 ◽  
Author(s):  
Namrata Anand ◽  
Tanmoy Chanda ◽  
Suvajit Koley ◽  
Sushobhan Chowdhury ◽  
Maya Shankar Singh
Keyword(s):  
Catalytic System ◽  
Direct Access ◽  
One Pot ◽  
Efficient Approach

A one-pot, efficient approach to quinoline synthesis, directly from 2-bromoaromatic aldehydes/ketones in a H2O–EtOH mixture involving a sequence of SNAr/reduction/annulation cascade using CuSO4-d-glucose, is devised.

Palladium-catalyzed [4 + 3] dearomatizing cycloaddition reaction of N-iminoquinolinium ylides

2020 ◽  
Vol 7 (18) ◽  
pp. 2612-2617
Author(s):  
Wenhao Dai ◽  
Chunpu Li ◽  
Yichu Liu ◽  
Xu Han ◽  
Xingjun Li ◽  
...  
Keyword(s):  
Functional Group ◽  
Cycloaddition Reaction ◽  
Membered Ring ◽  
Efficient Approach ◽  
Mild Conditions ◽  
Palladium Catalyzed

An efficient approach to obtain saturated seven-membered ring containing three heteroatoms has been developed by using a palladium-catalyzed [4 + 3] dearomatizing cycloaddition. This approach features mild conditions and good functional group tolerance.

scholarly journals TBAB-Catalyzed 1,6-Conjugate Sulfonylation of para-Quinone Methides: A Highly Efficient Approach to Unsymmetrical gem-Diarylmethyl Sulfones in Water

Molecules ◽  
2020 ◽  
Vol 25 (3) ◽  
pp. 539 ◽  
Author(s):  
Zhang-Qin Liu ◽  
Peng-Sheng You ◽  
Liang-Dong Zhang ◽  
Da-Qing Liu ◽  
Sheng-Shu Liu ◽  
...  
Keyword(s):  
Functional Group ◽  
Ammonium Bromide ◽  
Quinone Methides ◽  
Efficient Approach ◽  
Tetrabutyl Ammonium Bromide ◽  
Highly Efficient ◽  
Tetrabutyl Ammonium ◽  
Efficient Route ◽  
Addition Pathway

A highly efficient sulfonylation of para-quinone methides with sulfonyl hydrazines in water has been developed on the basis of the mode involving a tetrabutyl ammonium bromide (TBAB)-promoted sulfa-1,6-conjugated addition pathway. This reaction provides a green and sustainable method to synthesize various unsymmetrical diarylmethyl sulfones, showing good functional group tolerance, scalability, and regioselectivity. Further transformation of the resulting diarylmethyl sulfones provides an efficient route to some functionalized molecules.

An Atom-Economic and Stereospecific Access to Trisubstituted Olefins through Enyne Cross Metathesis Followed by 1,4-Hydrogenation

Synlett ◽  
2018 ◽  
Vol 29 (06) ◽  
pp. 785-792 ◽  
Author(s):  
Hans-Günther Schmalz ◽  
Friederike Ratsch
Keyword(s):  
Functional Group ◽  
Cross Metathesis ◽  
Broad Scope ◽  
Trisubstituted Olefins

The combination of intermolecular enyne cross metathesis and subsequent 1,4-hydrogenation opens a stereocontrolled and atom-economic access to trisubstituted olefins. By investigating different combinations of functionalized alkyne and alkene substrates, we found that the outcome (yield, E/Z ratio) of the Grubbs II-catalyzed enyne cross-metathesis step depends on the substrate’s structure, the amount of the alkene (used in excess), and the (optional) presence of ethylene. In any case, the 1,4-hydrogenation, catalyzed by 1,2-di­methoxybenzene-Cr(CO)3, proceeds stereospecifically to yield exclusively the E-products from both the E- and Z-1,3-diene intermediates obtained by metathesis. A rather broad scope and functional group compatibility of the method is demonstrated by means of 15 examples.

Sign in / Sign up

Export Citation Format

Share Document