Transition metal-free aroylation of NH-sulfoximines with methyl arenes

2015 ◽  
Vol 51 (80) ◽  
pp. 14889-14892 ◽  
Author(s):  
Ya Zou ◽  
Jing Xiao ◽  
Zhihong Peng ◽  
Wanrong Dong ◽  
Delie An
Keyword(s):  
Transition Metal ◽  
Organic Solvents ◽  
Metal Catalysts ◽  
Transition Metal Catalysts ◽  
Metal Free

An iodine-catalyzed N-aroylation of NH-sulfoximines with methyl arenes was herein demonstrated without participation of external organic solvents, transition metal-catalysts or ligands.

scholarly journals Transition-Metal-Free [3+2] Dehydration Cycloaddition of Donor-Acceptor Cyclopropanes With 2-Naphthols

2021 ◽  
Vol 9 ◽  
Author(s):  
Hua Zhao ◽  
Peng Shen ◽  
Dongru Sun ◽  
Hongbin Zhai ◽  
Yufen Zhao
Keyword(s):  
Transition Metal ◽  
Ring Opening ◽  
Metal Catalysts ◽  
Transition Metal Catalysts ◽  
Cyclization Reaction ◽  
Metal Free ◽  
Efficient Access ◽  
Donor Acceptor ◽  
Acid Catalyzed ◽  
Synthetic Application

A Brønsted acid-catalyzed domino ring-opening cyclization transformation of donor-acceptor (D-A) cyclopropanes and 2-naphthols has been developed. This formal [3+2] cyclization reaction provided novel and efficient access to the naphthalene-fused cyclopentanes in the absence of any transition-metal catalysts or additives. This robust procedure was completed smoothly on a gram-scale to afford the corresponding product with comparable efficiency. Furthermore, the synthetic application of the prepared product has been demonstrated by its transformation into a variety of synthetically useful molecules.

Recent advances in metal free- and late transition metal-catalysed hydroamination of unactivated alkenes

2015 ◽  
Vol 5 (4) ◽  
pp. 2017-2037 ◽  
Author(s):  
Elise Bernoud ◽  
Clément Lepori ◽  
Mohamed Mellah ◽  
Emmanuelle Schulz ◽  
Jérôme Hannedouche
Keyword(s):  
Transition Metal ◽  
Metal Catalysts ◽  
Transition Metal Catalysts ◽  
Late Transition Metal ◽  
Metal Free ◽  
Recent Advances ◽  
Late Transition

This Perspective article outlines some of the recent advancements in the development of (chiral) metal-free and late transition metal catalysts for hydroamination of unactivated alkenes.

Transition-Metal-Free Functionalization of Saturated and Unsaturated Amines to Bioactive Alkaloids Mediated by Sodium Chlorite

Synlett ◽  
2020 ◽  
Author(s):  
Fernando Sartillo-Piscil ◽  
Julio Romero-Ibañez ◽  
Lilia Fuentes
Keyword(s):  
Transition Metal ◽  
Precious Metals ◽  
Extraction Process ◽  
Metal Catalysts ◽  
Transition Metal Catalysts ◽  
Sodium Chlorite ◽  
Chemical Transformations ◽  
Metal Free ◽  
Cyclic Amines ◽  
Metal Catalyzed

AbstractNew approaches to the synthesis of alkaloids through the straightforward functionalization of C(sp3)–H and C(sp2)=C(sp2) bonds of simple five- and six-membered-ring N-heterocycles are highlighted. The direct functionalization of pre-existing N-heterocycles to advanced alkaloids intermediates is a chemical operation that commonly requires the intervention of transition or precious metals. Regardless the inherent unwanted waste production, the high economical cost of many transition-metal catalysts limits their use globally. Here, we account our efforts directed toward the synthesis of bioactive alkaloids under an economic and ecological fashion by using NaClO2 as the key activating or oxidizing reagent that substitutes the use of transition-metal catalysts. While undesired metal wastes are collected during the extraction process of a transition-metal-catalyzed reaction, innocuous NaCl is the commonly product waste when NaClO2 is employed in our chemical transformations. Beginning with the synthesis of 2,3-epoxyamides from allyl amines, we concluded with the functionalization of multiple and remote C(sp3)–H and C(sp3)–C(sp3) bonds in piperidine rings that enabled the preparation of important bioactive alkaloids. For the latter functionalization, a precise amount of co-oxidant reagent (NaOCl) and radical 2,2,6,6-tetramethylpiperidinyloxy (TEMPO) were needed.1 Introduction2 Direct Chemical Method for Preparing 2,3-Epoxyamides3 Dual C(sp3)–H Oxidation of Cyclic Amines to 3‑Alkoxyamine Lac­tams4 Electrochemical Deamination of 3-Alkoxyamine Lactams5 Direct C–H Oxidation of Piperazines and Morpholines to 2,3-Diketopiperazines and 3-Morpholinones, Respectively6 Transition-Metal-Free Triple C–H Oxidation7 Deconstructive Lactamization of Piperidines8 Conclusion

Schiff-base molecules and COFs as metal-free catalysts or silver supports for carboxylation of alkynes with CO2

2021 ◽  
Author(s):  
Lin Zhang ◽  
Ran Bu ◽  
Xiao-yan Liu ◽  
Peng-fei Mu ◽  
En-Qing Gao
Keyword(s):  
Schiff Base ◽  
Transition Metal ◽  
Co2 Fixation ◽  
Metal Catalysts ◽  
Transition Metal Catalysts ◽  
Terminal Alkynes ◽  
Metal Free ◽  
Mild Conditions

Carboxylating terminal alkynes with CO2 to produce propiolic acids is an atom-economic and high-value route for CO2 fixation and utilization, but the conversion under mild conditions needs transition metal catalysts....

Transition-metal-free direct perfluoroalkylation of quinoline amides at C5 position through radical cross-coupling under mild conditions

2017 ◽  
Vol 4 (6) ◽  
pp. 1116-1120 ◽  
Author(s):  
Jun Xu ◽  
Li Qiao ◽  
Beibei Ying ◽  
Xiaolei Zhu ◽  
Chao Shen ◽  
...  
Keyword(s):  
Transition Metal ◽  
Efficient Method ◽  
Cross Coupling ◽  
Metal Catalysts ◽  
Transition Metal Catalysts ◽  
Low Energy ◽  
Metal Free ◽  
Mild Conditions

A simple low-energy and efficient method is established for the synthesis of C5-selective perfluoroalkylation quinolines in the absence of any transition metal catalysts.

scholarly journals TBHP-mediated highly efficient dehydrogenative cross-oxidative coupling of methylarenes with acetanilides

2016 ◽  
Vol 12 ◽  
pp. 2250-2255 ◽  
Author(s):  
Cui Chen ◽  
Weibing Liu ◽  
Peng Zhou
Keyword(s):  
Transition Metal ◽  
Organic Solvents ◽  
Oxidative Coupling ◽  
Cross Coupling ◽  
Metal Catalysts ◽  
Transition Metal Catalysts ◽  
Coupling Method ◽  
Highly Efficient ◽  
Coupling Approach

A TBHP-mediated dehydrogenative cross-oxidative-coupling approach has been developed for the synthesis of N-arylbenzamides from methylarenes and acetanilides. This cross-coupling method is free of transition metal catalysts and ligands, and no extra organic solvents are required, which make it an useful and attractive strategy for the straightforward construction of C–N bonds. Besides, this conversion is an important complement to the conventional C–N forming strategies.

scholarly journals Direct alkylation of N,N-dialkyl benzamides with methyl sulfides under transition metal-free conditions

2021 ◽  
Vol 4 (1) ◽  
Author(s):  
Can-Can Bao ◽  
Hui-Zhen Du ◽  
Yan-Long Luo ◽  
Bing-Tao Guan
Keyword(s):  
Transition Metal ◽  
Functional Group ◽  
Metal Catalysts ◽  
Transition Metal Catalysts ◽  
Amide Bond ◽  
Selective Synthesis ◽  
Lithium Diisopropylamide ◽  
Organometallic Reagents ◽  
Metal Free ◽  
Resonance Stabilization

AbstractAmides are a fundamental and widespread functional group, and are usually considered as poor electrophiles owing to resonance stabilization of the amide bond. Various approaches have been developed to address challenges in amide transformations. Nonetheless, most methods use activated amides, organometallic reagents or transition metal catalysts. Here, we report the direct alkylation of N,N-dialkyl benzamides with methyl sulfides promoted by the readily available base LDA (lithium diisopropylamide). This approach successfully achieves an efficient and selective synthesis of α-sulfenylated ketones without using transition-metal catalysts or organometallic reagents. Preliminary mechanism studies reveal that the deprotonative aroylation of methyl sulfides is promoted by the directed ortho-lithiation of the tertiary benzamide with LDA.

scholarly journals One Pot and Metal-Free Approach to 3-(2-Hydroxybenzoyl)-1-aza-anthraquinones

Molecules ◽  
2019 ◽  
Vol 24 (16) ◽  
pp. 3017
Author(s):  
Jiaqi Yuan ◽  
Qian He ◽  
Shanshan Song ◽  
Xiaofei Zhang ◽  
Zehong Miao ◽  
...  
Keyword(s):  
Transition Metal ◽  
Functional Group ◽  
Metal Catalysts ◽  
Transition Metal Catalysts ◽  
Inert Gas ◽  
One Pot ◽  
Metal Free ◽  
Mild Conditions ◽  
Anthraquinone Derivatives

Herein, a direct strategy to synthesize 3-(2-hydroxybenzoyl)-1-aza-anthraquinones with excellent efficiency, mild conditions, and benign functional group compatibility was reported. A variety of 3-formylchromone compounds were employed as compatible substrates and this protocol gave the 3-(2-hydroxybenzoyl)-1-aza-anthraquinone derivatives in good to excellent yields without inert gas and expensive transition metal catalysts. Some compounds displayed good anti-proliferative activities.

scholarly journals An atom-economical addition of methyl azaarenes with aromatic aldehydes via benzylic C(sp3)–H bond functionalization under solvent- and catalyst-free conditions

2020 ◽  
Vol 16 ◽  
pp. 3093-3103
Author(s):  
Divya Rohini Yennamaneni ◽  
Vasu Amrutham ◽  
Krishna Sai Gajula ◽  
Rammurthy Banothu ◽  
Murali Boosa ◽  
...  
Keyword(s):  
Transition Metal ◽  
Aromatic Aldehydes ◽  
Metal Catalysts ◽  
Transition Metal Catalysts ◽  
Solvent Free ◽  
Practical Approach ◽  
Coupling Reagents ◽  
Bond Functionalization ◽  
Metal Free ◽  
Solvent Free Conditions

A convenient practical approach for the synthesis of 2-(pyridin-2-yl)ethanols by direct benzylic addition of azaarenes and aldehydes under catalyst- and solvent-free conditions is reported. This reaction is metal-free, green, and was carried out in a facile operative environment without using any hazardous transition metal catalysts or any other coupling reagents. Different aromatic aldehydes and azaarenes were monitored, and the yields of the resulting products were moderate to excellent. We accomplished several azaarene derivatives under neat conditions through a highly atom-economical pathway. To evaluate the preparative potential of this process, gram-scale reactions were performed up to a 10 g scale.

Metal-free nanostructured catalysts: Sustainable driving forces for organic transformations

2021 ◽  
Author(s):  
Behnam Gholipour ◽  
Salman Shojaei ◽  
Sadegh Rostamnia ◽  
Mohammad Reza Naimi-Jamal ◽  
Dokyoon Kim ◽  
...  
Keyword(s):  
Transition Metal ◽  
Heterogeneous Catalysts ◽  
Driving Forces ◽  
Nanostructured Catalysts ◽  
Metal Catalysts ◽  
Transition Metal Catalysts ◽  
Organic Transformations ◽  
Metal Free ◽  
The Past

Over the past few decades, research on heterogeneous catalysts, especially metal-free catalysts in industrial and research transformations, has intensified. Despite the obvious benefits of heterogeneous transition metal catalysts in quick...

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