Photo-induced 1,2-carbohalofunctionalization of C–C multiple bonds via ATRA pathway

2020 ◽  
Vol 18 (41) ◽  
pp. 8278-8293 ◽  
Author(s):  
Debojyoti Bag ◽  
Harpreet Kour ◽  
Sanghapal D. Sawant
Keyword(s):  
Efficient Method ◽  
Building Blocks ◽  
Atom Transfer ◽  
Atom Economy ◽  
Multiple Bonds ◽  
Radical Processes

Carbohalofunctionalization of C–C multiple bonds via atom transfer radical processes constitutes an efficient method for the construction of halogenated building blocks with complete atom economy. This review summarizes the recent advancements.

scholarly journals Aminoalkyl radicals as halogen-atom transfer agents for activation of alkyl and aryl halides

Science ◽  
2020 ◽  
Vol 367 (6481) ◽  
pp. 1021-1026 ◽  
Author(s):  
Timothée Constantin ◽  
Margherita Zanini ◽  
Alessio Regni ◽  
Nadeem S. Sheikh ◽  
Fabio Juliá ◽  
...  
Keyword(s):  
Halogen Atom ◽  
Building Blocks ◽  
Aryl Halides ◽  
Atom Transfer ◽  
Reduction Potentials ◽  
Tributyltin Hydride ◽  
Organic Halides ◽  
Wide Range ◽  
Carbon Carbon Bonds ◽  
Radical Processes

Organic halides are important building blocks in synthesis, but their use in (photo)redox chemistry is limited by their low reduction potentials. Halogen-atom transfer remains the most reliable approach to exploit these substrates in radical processes despite its requirement for hazardous reagents and initiators such as tributyltin hydride. In this study, we demonstrate that α-aminoalkyl radicals, easily accessible from simple amines, promote the homolytic activation of carbon-halogen bonds with a reactivity profile mirroring that of classical tin radicals. This strategy conveniently engages alkyl and aryl halides in a wide range of redox transformations to construct sp3-sp3, sp3-sp2, and sp2-sp2 carbon-carbon bonds under mild conditions with high chemoselectivity.

Insulating Composites Made from Sulfur, Canola Oil, and Wool

2020 ◽  
Author(s):  
Israa Bu Najmah ◽  
Nicholas Lundquist ◽  
Melissa K. Stanfield ◽  
Filip Stojcevski ◽  
Jonathan A. Campbell ◽  
...  
Keyword(s):  
Tensile Strength ◽  
Canola Oil ◽  
Building Blocks ◽  
Atom Economy ◽  
Flame Resistance ◽  
Sustainable Building ◽  
Second Stage ◽  
Wool Fibers ◽  
Insulating Properties ◽  
Polysulfide Polymer

An insulating composite was made from the sustainable building blocks wool, sulfur, and canola oil. In the first stage of the synthesis, inverse vulcanization was used to make a polysulfide polymer from the canola oil triglyceride and sulfur. This polymerization benefits from complete atom economy. In the second stage, the powdered polymer is mixed with wool, coating the fibers through electrostatic attraction. The polymer and wool mixture is then compressed with mild heating to provoke S-S metathesis in the polymer, which locks the wool in the polymer matrix. The wool fibers impart tensile strength, insulating properties, and flame resistance to the composite. All building blocks are sustainable or derived from waste and the composite is a promising lead on next-generation insulation for energy conservation.

Novel One-pot Synthesis of Pyranocarbazole Derivatives via an Isocyanide-based Three-component Reaction

2020 ◽  
Vol 17 ◽  
Author(s):  
Visarapu Malathi ◽  
Pedavenkatagari Narayana Reddy ◽  
Pannala Padmaja
Keyword(s):  
Efficient Method ◽  
Atom Economy ◽  
Reaction Conditions ◽  
One Pot ◽  
Catalyst Free ◽  
One Pot Synthesis ◽  
Three Component Reaction ◽  
High Yields

Abstract:: An efficient method has been developed for the synthesis of new pyrano[3,2-c] and pyrano[3,2-a]carbazole de-rivatives via a three component reaction of 4-hydroxycarbazole or 2-hydroxycarbazole, isocyanides, and dialkylacetylenedi-carboxylates. Noteworthy features of this protocol include mild reaction conditions, catalyst-free, high atom-economy and high yields.

Electrochemical Oxidative Esterification of Thiophenols: Efficient Access to Sulfinic Esters

2020 ◽  
Vol 17 (7) ◽  
pp. 540-547
Author(s):  
Chun-Hui Yang ◽  
Cheng Wu ◽  
Jun-Ming Zhang ◽  
Xiang-Zhang Tao ◽  
Jun Xu ◽  
...  
Keyword(s):  
Organic Synthesis ◽  
Efficient Method ◽  
High Efficiency ◽  
Building Blocks ◽  
Constant Current ◽  
Good Efficiency ◽  
Oxidative Esterification ◽  
Efficient Access ◽  
New Applications ◽  
Sulfinic Esters

Background: The sulfinic esters are important and useful building blocks in organic synthesis. Objective: The aim of this study was to develop a simple and efficient method for the synthesis of sulfinic esters. Materials and Methods: Constant current electrolysis from thiols and alcohols was selected as the method for the synthesis of sulfinic esters. Results and Discussion: A novel electrochemical method for the synthesis of sulfinic esters from thiophenols and alcohols has been developed. Up to 27 examples of sulfinic esters have been synthesized using the current methods. This protocol shows good functional group tolerance as well as high efficiency. In addition, this protocol can be easily scaled up with good efficiency. Notably, heterocycle-containing substrates, including pyridine, thiophene, and benzothiazole, gave the desired products in good yields. A plausible reaction mechanism is proposed. Conclusion: This research not only provides a green and efficient method for the synthesis of sulfinic esters but also shows new applications of electrochemistry in organic synthesis. It is considered that this green and efficient synthetic protocol used to prepare sulfinic esters will have good applications in the future.

Versatile procedure for site-specific grafting of polymer brushes on patchy particles via atom transfer radical polymerization (ATRP)

2016 ◽  
Vol 7 (16) ◽  
pp. 2858-2869 ◽  
Author(s):  
Bas G. P. van Ravensteijn ◽  
Willem K. Kegel
Keyword(s):  
Atom Transfer Radical Polymerization ◽  
Radical Polymerization ◽  
Polymer Brushes ◽  
Building Blocks ◽  
Atom Transfer ◽  
Site Specific ◽  
Patchy Particles

Combining chemically anisotropic colloids with Surface-Initiated ATRP enables for site-specific grafting of p(NIPAM) brushes. The resulting, partially grafted particles are employed as colloidal building blocks for finite-sized clusters.

An Efficient Method for the Preparation of Versatile Building Blocks: 1-Substituted 2,2-Dimethoxyethylamine Hydrochlorides

Synthesis ◽  
2009 ◽  
Vol 2009 (19) ◽  
pp. 3227-3232 ◽  
Author(s):  
Xinyan Wang ◽  
Yuefei Hu ◽  
Bo Liu ◽  
Deyong Su ◽  
Guolin Cheng ◽  
...  
Keyword(s):  
Efficient Method ◽  
Building Blocks

scholarly journals Regioselective Monobromination of Phenols with KBr and ZnAl–BrO3−–Layered Double Hydroxides

Molecules ◽  
2020 ◽  
Vol 25 (4) ◽  
pp. 914
Author(s):  
Ligeng Wang ◽  
Chun Feng ◽  
Yan Zhang ◽  
Jun Hu
Keyword(s):  
Efficient Method ◽  
Layered Double Hydroxides ◽  
Atom Economy ◽  
Reaction Condition ◽  
Double Hydroxides ◽  
Para Site

The regioselective mono-bromination of phenols has been successfully developed with KBr and ZnAl–BrO3−–layered double hydroxides (abbreviated as ZnAl–BrO3−–LDHs) as brominating reagents. The para site is much favorable and the ortho site takes the priority if para site is occupied. This reaction featured with excellent regioselectivity, cheap brominating reagents, mild reaction condition, high atom economy, broad substrate scope, and provided an efficient method to synthesize bromophenols.

The dual-catalyzed boryldifluoroallylation of alkynes: an efficient method for the synthesis of skipped gem-difluorodienes

2020 ◽  
Vol 56 (15) ◽  
pp. 2340-2343 ◽  
Author(s):  
Kai-Feng Zhuo ◽  
Wen-Yan Xu ◽  
Tian-Jun Gong ◽  
Yao Fu
Keyword(s):  
Efficient Method ◽  
Building Blocks

The Cu/Pd-catalyzed boryldifluoroallylation of alkynes was achieved, providing the skipped gem-difluorodiene scaffolds with high regio- and stereoselectivity. An array of synthetic building blocks can be obtained via further transformations.

scholarly journals Sustainable Access to π-Conjugated Molecular Materials via Direct (Hetero)Arylation Reactions in Water and under Air

Molecules ◽  
2020 ◽  
Vol 25 (16) ◽  
pp. 3717
Author(s):  
Adiel Mauro Calascibetta ◽  
Sara Mattiello ◽  
Alessandro Sanzone ◽  
Irene Facchinetti ◽  
Mauro Sassi ◽  
...  
Keyword(s):  
Reaction Medium ◽  
Building Blocks ◽  
High Yield ◽  
Coupling Reactions ◽  
Materials Chemistry ◽  
Atom Economy ◽  
Reaction Conditions ◽  
Cross Coupling Reactions ◽  
High Boiling Point ◽  
Yield And Purity

Direct (hetero)arylation (DHA) is playing a key role in improving the efficiency and atom economy of C–C cross coupling reactions, so has impacts in pharmaceutical and materials chemistry. Current research focuses on further improving the generality, efficiency and selectivity of the method through careful tuning of the reaction conditions and the catalytic system. Comparatively fewer studies are dedicated to the replacement of the high-boiling-point organic solvents dominating the field and affecting the overall sustainability of the method. We show herein that the use of a 9:1 v/v emulsion of an aqueous Kolliphor 2 wt% solution while having toluene as the reaction medium enables the preparation of relevant examples of thiophene-containing π-conjugated building blocks in high yield and purity.

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