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This article provides an overview of recent advancements in transition-metal-catalyzed Sonogashira cross-coupling reactions of alkyl electrophiles. It discusses the challenges associated with coupling nonactivated alkyl electrophiles and highlights three catalytic systems that have been developed to address these challenges. The article also mentions the development of enantioselective Sonogashira reactions using copper catalysts with chiral ligands. The challenges and future directions in this field are also discussed. [Extracted from the article]

This article explores the use of copper complexes as catalysts for radical reactions in organic synthesis. It emphasizes the importance of metal-catalyzed processes in drug development and highlights copper's suitability as a catalyst due to its low cost and availability. The role of ligands in stabilizing copper complexes and influencing their reactivity is also discussed. The authors specifically focus on copper-catalyzed radical cross-coupling reactions and direct alkylation of electron-rich heteroarenes. The article provides detailed information on reaction mechanisms and the broad scope and efficiency of these reactions. Additionally, the authors explore the use of copper complexes in photoinduced radical reactions as an alternative to traditional photoredox catalysts. The challenges and future prospects of copper catalysis in radical chemistry are also addressed, with an emphasis on the advantages of using copper complexes and their potential for developing new radical reactions and processes. [Extracted from the article]

This document provides information on the synthesis of a COVID-19 therapeutic drug called Ensitrelvir. The addition of LiCl (lithium chloride) was found to facilitate the generation of lithium triazinolate, which improved the yield and selectivity of the N-alkylation process. The use of LiCl and Et3N (triethylamine) also simplified the work-up operation and allowed for the use of a cheaper and more readily available base. The method was effective for various electrophiles, and further investigation is being conducted on the substrate scope of nucleophiles. The document also includes information on the physical and spectroscopic properties of the synthesized compounds, as well as acknowledgments and additional supporting information. [Extracted from the article]

This article discusses the synthesis and characterization of several compounds, including piperazinone derivatives. The compounds are described in terms of their chemical structures, physical properties, and spectroscopic data. The authors provide detailed information about the synthesis procedure, yield, and characterization techniques used. This information can be useful for researchers studying these specific compounds or related topics. The authors acknowledge the University of Belgrade, Faculty of Pharmacy for their support, and additional supporting information is available online. [Extracted from the article]

In this paper, we report an alternative approach to the targeted -oxyallylboronate: a copper-catalyzed 1,4-acylboration of , -unsaturated esters with B SB 2 sb pin SB 2 sb and pivalic anhydride is described (Scheme 1c). H SB 2 sb O SB 2 sb under acetate buffer conditions [11] furnished the corresponding allylic alcohol B 4 b with maintenance of the ketene acetal moiety, which can be a good synthetic handle for further manipulations. The ligand gave a large impact on the yield and I E/Z i selectivity, with the electron-withdrawing monodentate P(3,5-(CF SB 3 sb ) SB 2 sb C SB 6 sb H SB 3 sb ) SB 3 sb proving to be best (entries 1-5). Keywords: allylboronate; borylation; conjugate addition; copper; stereoselectivity EN allylboronate borylation conjugate addition copper stereoselectivity 2205 2209 5 10/31/23 20231127 NES 231127 Graph Allylborons constitute an important class of organoboron compounds in modern synthetic organic chemistry because they enable the chemo- and stereoselective allylation of organic molecules, after which the resulting allyl moiety can be transformable with high diversity. [Extracted from the article]

This document provides an overview of recent developments in the synthesis and transformation of ¿-haloboron compounds, which are important building blocks in organic synthesis. The authors discuss various methods for preparing ¿-haloboron compounds, such as the Matteson homologation reaction and hydrozirconation. They also highlight the use of nickel catalysts for the asymmetric transformation of racemic ¿-haloboronates. The document concludes by discussing a new method for constructing ¿-haloboronates through a deoxygenative difunctionalization of carbonyls. The authors emphasize the need for further research in this area and share their own findings in the field. [Extracted from the article]

[34] The reaction with enantioenriched -methylbenzylboronic acid pinacol ester resulted in a 56:44 diastereomeric mixture of alcohol products B 48 b , the same diastereomeric mixture as was observed using racemic alkylboronic ester. [3][5][6] This short review details our laboratory's examination of reactions using benzylboronic acid pinacol ester and secondary and tertiary benzylboronic esters as nucleophiles. Keywords: boron; benzylation; Lewis base; copper; boronate EN boron benzylation Lewis base copper boronate 2639 2647 9 08/17/23 20230901 NES 230901 Graph 1 Introduction Organoboranes have found great utility in organic synthesis. Specifically, substrates containing esters and amides to the ketone were found to be compatible under these reaction conditions with no reaction being observed at the ester or amide carbonyl carbon ( B 25 b and B 26 b ). [Extracted from the article]

IR (C SB 2 sb H SB 2 sb Cl SB 2 sb ): 1675, 1620 cm SP -1 sp . This had also been observed for deoxyhalogenation reactions using Ph SB 3 sb PX SB 2 sb reagents in the presence of triethylamine. This transformation is already well-documented: COCl SB 2 sb , PCl SB 3 sb , OPCl SB 3 sb , acetyl and oxalyl chlorides, triphenylphosphine-derived reagents Ph SB 3 sb PX SB 2 sb , Ph SB 3 sb P/CX SB 4 sb and the Vilsmeier reagent have been successfully used. 3-Chloro-6-allylcyclohex-2-en-1-one (21a) 1518 The title product was prepared using 0.183 g (1.4 mmol) of TMCE ( B 2a b ) and 0.189 g (1.2 mmol) of 4-allylcyclohexan-1,3-dione in CH SB 2 sb Cl SB 2 sb for 5 h at rt. [Extracted from the article]

The reduction of alkyl chlorides using triethylsilane is investigated. Primary, secondary, tertiary, and benzylic C–Cl bonds are effectively converted into C–H bonds using an [IrCl(cod)]2 /2,6-bis(benzimidazol-2′-yl)pyridine catalyst system. This catalyst system is quite simple since the tridentate N-ligand can be easily prepared in one step from commercially available reagents. [ABSTRACT FROM AUTHOR]

Chiral-auxiliary-mediated synthesis represents the most frequently used synthetic tool for the induction of chirality on α-position of γ-lactams in organic synthesis. However, the general strategy requires the stoichiometric use of chiral reagents with multiple manipulation steps. Transition-metal-catalyzed asymmetric alkene dicarbofunctionalization using readily available substrates under mild conditions allows the simultaneous construction of two vicinal chemical bonds and a chiral carbon center, hence, gain expedient access to chiral heterocycles. Herein, we disclose a Ni-catalyzed enantioselective reaction of 3-butenyl carbamoyl chloride and primary alkyl iodide enabled by a newly designed chiral 8-quinoline imidazoline ligand (8-Quinim). This protocol features broad functional group tolerance and high enantioselectivities, achieving unprecedented synthesis of chiral nonaromatic heterocycles via catalytic reductive protocol. 1 Introduction 2 Development of 8-Quinim Ligand 3 Nickel/8-Quinim-Catalyzed Enantioselective Synthesis of Chiral α-Alkylated γ-Lactam 4 Conclusion and Outlook [ABSTRACT FROM AUTHOR]

Nonactivated alkyl chlorides are readily available and bench-stable feedstocks; however, they exhibit an inherent chemical inertness, in part, due to their large negative reduction potentials, which have precluded their widespread use as radical precursors in visible-light photocatalysis. Herein, we highlight some recent strategies for activating challenging organic halides under light irradiation, with special emphasis in C(sp3)–halide bonds. In this line, a brief summary of the reactivity of Vitamin B12 , F430 cofactor and derivatives is required to comprehend the chemistry behind our developed Cu/M (M = Co, Ni) dual catalytic system. Catalyst design has been key for developing a mild and general photoredox methodology for the intramolecular reductive cyclization of nonactivated alkyl chlorides with tethered alkenes. The cleavage of strong C(sp3)–Cl bonds is mediated by a highly nucleophilic low-valent cobalt or nickel intermediate generated by visible-light photoredox reduction employing a copper photosensitizer. [ABSTRACT FROM AUTHOR]

A cobalt-N-heterocyclic carbene catalytic system promotes pyridine-directed olefinic C-H alkylation reactions using a variety of primary and secondary alkyl chlorides under mild conditions. Radical clock experiments suggest that the reaction involves single-electron transfer from the cobalt intermediate to the alkyl chloride. [ABSTRACT FROM AUTHOR]

Alkyl aryl ketones were prepared on a gram scale by the nickel-catalyzed reductive coupling of alkyl iodides with aroyl chlorides. When scaled up 30-fold, this reaction shows a comparable coupling efficiency to the previously reported reaction performed under smallscale conditions. The mild and convenient reaction conditions show excellent tolerance to a range of functional groups and provide the ketones in good to excellent yields [ABSTRACT FROM AUTHOR]

Secondary alkyl chlorides have been efficiently prepared from secondary alkyl sulfonates under mild and user-friendly conditions. The exchange reaction was generally performed by using benzyltributylammonium chloride in acetone (reflux, 30 min). Yields are excellent from functionalized, base-sensitive and hindered secondary alkyl sulfonates [ABSTRACT FROM AUTHOR]

A batchwise, multigram preparation of 2-azabicyclo- [2.1.1]hexane hydrochloride (1·HCl) was developed, delivering a total of 195 grams of material. The key synthetic step involves an intramolecular displacement of a primary alkyl chloride with a tert-butylsulfinamide to forge the [2.1.1]-bicyclic ring system. [ABSTRACT FROM AUTHOR]

A cyclic glycerophospholipid, in which two glycerols are connected via alkyl chains to form a 64-membered macrocycle, was synthesized. The structural features that differentiate this from our analogous lipids previously reported are two methylene moieties in the alkyl chains, which were incorporated to improve membrane fluidity. Fluorescence recovery after photobleaching revealed that the membranes made from the methylene-containing cyclic lipid demonstrated fluidity at room temperature unlike those of a linear alkyl-chain lipid of equal ring size. [ABSTRACT FROM AUTHOR]

The article presents abstracts on topics related to studies on cyclopropenium ion including the conversion of alcohols into alkyl chlorides, the Beckmann rearrangement of ketoximes, and the development of cyclopropenium ion activated cyclodehydration of 1,4- and 1,5-diols.

A correction to the article "Cobalt-Catalyzed Directed Alkylation of Olefinic C-H Bond with Primary and Secondary Alkyl Chlorides" that was published in the previous issue is presented.