Nickel-Catalyzed Enantioselective Coupling of Acid Chlorides with α-Bromobenzoates: An Asymmetric Acyloin Synthesis

Journal of the American Chemical Society, Journal Year: 2022, Volume and Issue: 144(50), P. 23019 - 23029

Published: Dec. 8, 2022

The reaction of common acyl-metal species (acyl anion) with aldehydes to furnish acyloins has received much less attention and specifically was restricted using preformed stoichiometric reagents. Moreover, the (catalytic) enantioselective variants remain unexplored, asymmetric synthesis chiral met significant challenges in organic synthesis. Here, we uncover highly coupling acid chlorides α-bromobenzoates by nickel catalysis for producing enantioenriched protected α-hydroxy ketones (acyloins, >60 examples) high enantioselectivities (up 99% ee). successful execution this protocol enables formation a key ketyl radical from α-bromoalkyl benzoate situ generated corresponding aldehyde acyl bromide, which finally is captured acyl-Ni catalytically formed chlorides, thus avoiding use synthetic utility chemistry demonstrated downstream elaboration toward diverse set synthetically valuable building blocks biologically active compounds.

Language: Английский

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Ni-catalyzed carbamoylation of unactivated alkenes for stereoselective construction of six-membered lactams

Nature Communications, Journal Year: 2022, Volume and Issue: 13(1)

Published: Oct. 10, 2022

Abstract Nitrogen-based heterocycles have aroused widespread interest due to their reoccurrence in many pharmaceuticals. Amongst these motifs, the enantioenriched lactams are ubiquitous scaffolds found myriad biologically active natural products and drugs. Recently, transition metal-catalyzed asymmetric carbamoylation has been widely employed as a straightforward arsenal for chiral lactam architecture synthesis, including β-lactam γ-lactam. However, despite extensive efforts, there still remains no protocol accomplish related δ-lactam synthesis. In this manuscript, Ni-catalyzed enantioselective of unactivated alkenes by leverage reductive dicarbofunctionalization strategy allows expedient access two types mostly common six-membered lactams: 3,4-dihydroquinolinones 2-piperidinone high yield enantioselectivity. This features with good functional group tolerance, well broad substrate scope. The newly developed 8-Quinox skeleton ligand is key parameter transformation, which significantly enhances reactivity

Language: Английский

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Ketones from aldehydes via alkyl C(sp3)−H functionalization under photoredox cooperative NHC/palladium catalysis

Nature Communications, Journal Year: 2023, Volume and Issue: 14(1)

Published: July 8, 2023

Direct synthesis of ketones from aldehydes features high atom- and step-economy. Yet, the coupling with unactivated alkyl C(sp3)-H remains challenging. Herein, we develop via functionalization under photoredox cooperative NHC/Pd catalysis. The two-component reaction iodomethylsilyl ether gave a variety β-, γ- δ-silyloxylketones 1,n-HAT (n = 5, 6, 7) silylmethyl radicals to generate secondary or tertiary following ketyl NHC three-component addition styrenes corresponding ε-hydroxylketones generation benzylic by radicals. This work demonstrates radical catalysis, provides two three component reactions for functionalization. synthetic potential this protocol was also further illustrated late-stage natural products.

Language: Английский

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Nickel/Quinim Enabled Asymmetric Carbamoyl‐Acylation of Unactivated Alkenes

Chinese Journal of Chemistry, Journal Year: 2023, Volume and Issue: 41(14), P. 1673 - 1678

Published: Feb. 14, 2023

Comprehensive Summary Transition metal‐catalyzed difunctionalization of tethered alkene has emerged as a prevailing tool for the expedient construction synthetically valuable cyclic compounds. However, most efforts have been devoted to reaction styrene‐type substrates due their rigid scaffold and high reactivity. With respect nonaromatic olefin, especially mono‐substituted alkene, still remains largely underdeveloped. Herein, we disclose nickel/Quinim complex TBADT‐cocatalyzed asymmetric carbamoyl‐acylation unactivated on carbamoyl chlorides with diverse aldehydes. The exhibits broad substrate scope good functional group tolerance, well efficiency enantioselectivity. Both monosubstituted 1,1‐substituted alkenes can work either aliphatic or aromatic aldehydes under current protocol, providing convenient access an array medicinally useful chiral γ‐lactams derivatives bearing convertible acyl functionality. This showcases more application possibilities Quinim ligand in future catalytic transformations.

Language: Английский

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Three-Component Ni-Catalyzed Silylacylation of Alkenes

ACS Catalysis, Journal Year: 2021, Volume and Issue: 11(3), P. 1858 - 1862

Published: Jan. 26, 2021

A Ni-catalyzed silylacylation of alkenes is presented. The reaction combines alkenes, ClZnSiR3, and acid chlorides to provide rapid access β-silyl ketones. Importantly, the method involves a [Ni]-SiR3 complex as catalytic intermediate, which rarely described for three-component alkene functionalization. Finally, synthetic utility products demonstrated, mechanistic details are described.

Language: Английский

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Pd-Catalyzed Ring-Closing/Ring-Opening Cross Coupling Reactions: Enantioselective Diarylation of Unactivated Olefins

ACS Catalysis, Journal Year: 2021, Volume and Issue: 11(14), P. 8942 - 8947

Published: July 7, 2021

Pd-catalyzed chemo-, regio-, and enantioselective ring-closing/ring-opening cross coupling reaction has been developed with diverse aryl halide-tethered alkenes benzocyclobutenols as substrates, which renders the highly diarylation of unactivated provides a convenient method toward chiral 2,3-dihydrobenzofurans bearing quaternary stereocenter excellent enantioselectivities (up to 98% ee). The application in concise synthesis analogue cannabinoid receptor 2 agonists is described.

Language: Английский

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Recent advances in transition metal-catalyzed reactions of carbamoyl chlorides

Organic Chemistry Frontiers, Journal Year: 2021, Volume and Issue: 8(14), P. 4024 - 4045

Published: Jan. 1, 2021

This review highlights the recent advancements of carbamoyl chlorides in transition metal-catalyzed reactions to access various amide-containing molecules and heterocycles.

Language: Английский

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Organic reactions in aqueous media catalyzed by nickel

Green Chemistry, Journal Year: 2021, Volume and Issue: 23(17), P. 6273 - 6300

Published: Jan. 1, 2021

This review highlights the nickel-catalyzed organic reactions in aqueous media with special focus on mechanistic course of catalytic and their applications.

Language: Английский

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Recent Advances in C–F Bond Activation of Acyl Fluorides Directed toward Catalytic Transformation by Transition Metals, N-Heterocyclic Carbenes, or Phosphines

Synthesis, Journal Year: 2022, Volume and Issue: 54(17), P. 3667 - 3697

Published: May 6, 2022

Abstract Numerous studies on the activation of carbon–fluorine bonds have been reported in recent years. For example, acyl fluorides utilized as versatile reagents for acylation, arylation, and even fluorination. In this review, we focus compounds with bonds, highlight advances strategies their C–F via transition-metal catalysis, N-heterocyclic carbene (NHCs) organophosphine classical nucleophilic substitution reactions. 1 Introduction 2 Transition-Metal-Mediated Bond Activation 2.1 Acylation (Carbonyl-Retentive) Coupling Reactions 2.2 Decarbonylative 2.3 by Other Transition Metals 3 N-Heterocyclic Carbenes 3.1 NHC-Catalyzed Cycloaddition Acyl Fluorides 3.2 Radical Functionalization 3.3 Nucleophilic Fluorination (Hetero)aromatics 4 Phosphines 4.1 Phosphine-Catalyzed Direct 4.2 Indirect 5 Classical Substitution 6 Miscellaneous Examples 7 Summary Perspective

Language: Английский

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Nickel-Catalyzed Reductive Asymmetric Aryl-Acylation and Aryl-Carbamoylation of Unactivated Alkenes

CCS Chemistry, Journal Year: 2021, Volume and Issue: 4(5), P. 1510 - 1518

Published: May 13, 2021

Open AccessCCS ChemistryCOMMUNICATION1 May 2022Nickel-Catalyzed Reductive Asymmetric Aryl-Acylation and Aryl-Carbamoylation of Unactivated Alkenes Youxiang Jin, Pei Fan Chuan Wang Jin Hefei National Laboratory for Physical Science at the Microscale Department Chemistry, University Technology China, Hefei, Anhui 230026 , School Chemical Materials Engineering, Huainan Normal University, Huainan, 232038 *Corresponding author: E-mail Address: [email protected] Center Excellence in Molecular Synthesis CAS, https://doi.org/10.31635/ccschem.021.202101040 SectionsSupplemental MaterialAboutAbstractPDF ToolsAdd to favoritesDownload CitationsTrack Citations ShareFacebookTwitterLinked InEmail Herein we report a nickel-catalyzed asymmetric two-component reductive aryl-acylation aryl-carbamoylation aryl-iodide-tethered unactivated alkenes, which utilize ortho-pyridinyl esters isocyanates as electrophilic acyl sources, respectively. Under catalysis nickel–pyrox complex with zinc powder reductant, variety chiral indanes, indolines, dihydrobenzofurans bearing quaternary stereogenic center were prepared moderate high efficiency good excellent enantioselectivities. The utility this method is demonstrated by various simple derivatizations attached carbonyl group, particularly sequential benzylic oxidation pinacol coupling, provide concise entry benzene-fused bicyclic bridged ring framework containing three challenging tetrasubstituted stereocenters stereocontrol. Download figure PowerPoint Introduction In last decade, transition metal-catalyzed enantioselective dicarbofunctionalizations tethered alkenes have evolved into reliable construct scaffold cyclic compounds.1–6 majority these reactions rely on facially selective Heck-type arylmetallation pendant olefinic unit enantiodetermining step,7 followed trapping generated σ-alkyl metal species either nucleophile or an electrophile. Based strategy, aryl-alkylation,8–10 diarylation,10–13 aryl-benzylation,14 aryl-alkenylation,15,16 aryl-alkynylation13,17,18 incorporated been developed under palladium, copper, nickel catalysis. As important subset dicarbofunctionalization reactions, olefin allows synthesis structurally compounds directly starting from considerable progress has accomplished domain.19–34 However, variants are still rare.31–34 2012, Dong et al.31 reported one-component version employing strained benzocyclobutanones precursors, was efficiently catalyzed rhodium (Figure 1a, equation 1). recent years, Correia32 Guan33 palladium-catalyzed carbonylative Heck using carbon monoxide combination aryl boronic acids anilines terminating agents, providing series highly enantioenriched carbonyl-containing oxindoles 2). Very recently, Ye co-workers34 described aryl-carbamoylation, successfully converted carbamoyl-fluoride-tethered wide range γ-lactams manner 3). Figure 1 | alkenes. aforementioned general approaches redox-neutral reaction pathway plagued one more following disadvantages: (1) requirement preformation organometallics; (2) cost noble (rhodium palladium) catalyst; (3) use toxic odorless gas, arguably undesirable laboratory scale synthesis; (4) basic conditions leading incompatibility base-sensitive functionalities. To address issues mentioned above, turned our attention establish strategy35–42 that could avoid pregenerated organometallics earth-abundant catalyst base-free conditions. We envisioned target would be achieved via appropriate source coupling partner aryl-halide-tethered stoichiometric reductant. This reductant offer new prepare benzene-annulated synthetically useful group fashion 1b). Results Discussion Optimization First, focused development aryl-acylation. realize reaction, initially screened acylating agents including ester 2a,43,44 acid chloride 2a- 1,45–50 fluoride 2,51 anhydride 3,52–54 thioester 4,55,56 activated amide 5,57 proven successful different cross-electrophile reactions43–57 (Table These alkene 1a performed DMA 40 °C NiBr2·glyme precatalyst, Pyrox L1 ligand, Zn best outcome terms both induction case 2a wherein desired product 3aa obtained 25% yield 95% ee. Table Preliminary Screening Electrophilic Acylating Agentsa–c aUnless otherwise specified, 0.2 mmol 2.0 equiv 2a–2a- 5, 10 mol % NiBr2·glyme, 15 0.5 mL 12 h. bYields isolated through column chromatography. cEnantiomeric excesses determined High-Performance Liquid Chromatography (HPLC) analysis stationary phase. Encouraged initial results, continued optimize varying parameters improve efficiency, first conducted higher temperature. Indeed, elevated 31% while enantioselectivity remained (Entry Subsequently, ligands examined studied (Entries 2–10). general, bis(oxazoline) (BiOX) L2– 8 able promote yields enantiomeric ranging 89% 2–8). contrast, bis(oxazoline)-pyridine (PyBOX) L9 phosphine–oxazoline (PHOX) L10 ligand failed deliver compound 9 10). Next, several Ni(II) salts bis(cyclooctadiene)nickel(0) (Ni(COD)2) surveyed 11–14), highest NiBr2·diglyme 14). case, also increased 38%. Although Ni(COD)2 gave yield, excess diminished 92% 13). At juncture, decided carry out 2 propensity undergo dimerization after cyclization. Gratifyingly, improved 61% based o-pyridinyl 15). A brief solvent screening undertaken, no better result provided 16–18). Performing 80 resulted but declined level 19). Replacing Mn reducing agent led inferior 20). Moreover, bromo analog precursor 3aa, albeit much lower 21). Reaction Conditionsa Entry Ligand Ni-precatalyst Solvent Yield (%)b ee (%)c 31 95 L2 27 55 3 L3 29 63 4 L4 24 5 L5 trace n.d.d 6 L6 11 89 7 L7 26 72 L8 35 0 – NiBr2 NiCl2 30 13 50 92 14 38 96 15e NiBr2· diglyme 61 16e DMF 41 17e NMP 60 94 18e THF 19 19e,f 64 20e,g 16 88 21h 32 2a, Ni-precatalyst, L cDetermined HPLC dNot determined. eThe preformed 1a. fThe °C. gMn used instead Zn. hThe analogue (2 equiv) Substrate scope After establishing optimum conditions, started investigate substrate Ni-catalyzed array benzoates n electron-donating electron-withdrawing substitution positions reacted standard delight, all proceeded smoothly, furnishing products 3aa– Of note organometallics- ( 3ah– am) nitrile 3an) moieties well tolerated, not previous arylboronic conditions.32,33 Furthermore, naphthoate posed problem, 3ao excess. 2-furonate 2p, -thiophenecarboxylate 2q, indole-2-carboxylate 2r proved pertinent enabling incorporation heterocycles backbone 3ap– ar) induction. Unfortunately, formed when alkanoates utilized precursors. Evaluation Scope Aryl-Acylationa–c 1, NiBr2·diglyme, dThe 4-mmol 2a. varied structure No significant impact observed increasing bulkiness geminal 3bd, 3bm, 3cd). Either groups introduced phenyl iodides, yielding 3fd, 3fm, 3gd, 3gm enantiocontrol. applicable construction indoline 3hd– jd) decreasing ascending N-substitution noticed. addition, simply scaled up mmol, affording 60% 94% introduce carbamoyl moiety across unit. chlorides unsuccessful. however, isocyanates58–60 competitive carbamoylating catalytic system slightly modified explored, results summarized 4. accommodated, benzamides 5aa– ak excesses. Notably, keto intact during reaction. aliphatic precursors products. On other hand, broad allowed efficient 5ba– oa) enantioselectivities most cases. Aryl-Carbamoylationa–c 1.5 4, L1, 1.0 NEt3 without NEt3. Derivatization cross-coupling demonstrate method, aryl-carbonylation subjected Wittig olefination, delivering 71% meta-Chloroperoxybenzoic (mCPBA)-mediated Baeyer–Villiger smoothly corresponding phenolic 64% yield. hydrolysis afforded carboxylic 88% present core GPR40 agonists61 ruthenium-catalyzed indane furnished set indanones yields.62 Taking advantage two 9, transformed them diverse rings centers diastereocontrol samarium-mediated intramolecular pinacol-coupling 2b).63 Besides, reduction 5aa LiAlH4 amine 75% 2c). one-pot aza-annulation styrene DDQ-mediated enabled installation quinolone onto 12) 2d).64 Derivatizations (a) mCPBA (10 equiv), para-toluenesulfonic monohydrate (pTsOH•H2O) (1 dichloroethane (DCE), °C, (b) LiOH (5 MeOH/H2O = 10:1, 45 (c) RuCl3 (0.16 %), iodide (PhI) oxone MeCN/H2O (1:1), room temperature, (d) Samarium (Sm) (1.2 trimethylsilyl THF, 67 20 Proposed mechanism basis reports,12,14,65 proposed plausible Initially, Ni(0) condition, underwent oxidative addition 1. resultant I arylnickelation unit, accomplish stereocenter. Zn-mediated intermediate II delivered Ni(I) III, addition. Facile elimination Ni(III) IV 3. Finally, o-pyridinylate V reduced Zn, regenerate next cycle. III migratory insertion C–N double bond install moiety. Reduction VI protonation completion yielded 5. mechanism. Conclusion conclusion, carbonylating agent, Ni/Pyrox key step. By circumventing organometallics, strong bases, functionality tolerance. further Particularly, stereocontrol oxidation/pinacol-coupling sequence. Supporting Information available includes experimental procedures, characterization data, 1H NMR, 13C 19F chromatograms (PDF). Conflict Interest authors declare competing interests. Acknowledgments work supported start-up funds Young Scholar 1000 Talents Plan, Natural Foundation China (21772183 22071230), Fundamental Research Funds Central Universities (WK2060190086), Project Funded Postdoctoral (2020M682006), China. References Giri R.; Shekhar K. 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Huang Y.-H.; S.-R.; D.-P.; P.-Q.Intermolecular Dehydrative [4 + 2] Aza-Annulation N-Arylamides Divergent Entrance Aza-Heterocycles.Org. 1681–1685. 65. 6989–6994. Previous articleNext article FiguresReferencesRelatedDetails Issue AssignmentVolume 4Issue 5Page: 1510-1518Supporting Copyright & Permissions© 2021 Chinese SocietyKeywordsnickelreductive cross-couplingacylationcarbamoylationdicarbofunctionalizationAcknowledgmentsThis Downloaded 1,942 times PDF DownloadLoading ...

Language: Английский

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