Enantioselective Ni-Catalyzed Electrochemical Synthesis of Biaryl Atropisomers

Journal of the American Chemical Society, Journal Year: 2020, Volume and Issue: 142(22), P. 9872 - 9878

Published: May 11, 2020

A scalable enantioselective nickel-catalyzed electrochemical reductive homocoupling of aryl bromides has been developed, affording enantioenriched axially chiral biaryls in good yield under mild conditions using electricity as a reductant an undivided cell. Common metal reductants such Mn or Zn powder resulted significantly lower yields the absence electric current otherwise identical conditions, underscoring enhanced reactivity provided by combination transition catalysis and electrochemistry.

Language: Английский

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Organic Synthesis Using Nitroxides

Chemical Reviews, Journal Year: 2023, Volume and Issue: 123(16), P. 10302 - 10380

Published: Aug. 14, 2023

Nitroxides, also known as nitroxyl radicals, are long-lived or stable radicals with the general structure R1R2N–O•. The spin distribution over nitroxide N and O atoms contributes to thermodynamic stability of these radicals. presence bulky N-substituents R1 R2 prevents radical dimerization, ensuring their kinetic stability. Despite reactivity toward various transient C some nitroxides can be easily stored under air at room temperature. Furthermore, oxidized oxoammonium salts (R1R2N═O+) reduced anions (R1R2N–O–), enabling them act valuable oxidants reductants depending on oxidation state. Therefore, they exhibit interesting across all three states. Due fascinating properties, find extensive applications in diverse fields such biochemistry, medicinal chemistry, materials science, organic synthesis. This review focuses versatile For use other important fields, we will refer several articles. introductory part provides a brief overview history chemistry. Subsequently, key methods for preparing discussed, followed by an examination structural diversity physical properties. main portion this is dedicated reactions, wherein parent corresponding serve active species. It demonstrated that functional groups (such alcohols, amines, enolates, alkanes among others) efficiently oxidized. These oxidations carried out using catalysts combination stoichiometric terminal oxidants. By reducing anions, become effective reagents intriguing Nitroxides possess ability selectively react making useful terminating cascade reactions forming alkoxyamines. Depending structure, alkoxyamines weak C–O bonds, allowing thermal generation through reversible bond cleavage. Such thermally generated participate transformations, discussed end review. application strategy natural product synthesis presented.

Language: Английский

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Boryl Radical Activation of Benzylic C–OH Bond: Cross-Electrophile Coupling of Free Alcohols and CO₂ via Photoredox Catalysis

Journal of the American Chemical Society, Journal Year: 2022, Volume and Issue: 144(19), P. 8551 - 8559

Published: April 4, 2022

A new strategy for the direct cleavage of C(sp3)-OH bond has been developed via activation free alcohols with neutral diphenyl boryl radical generated from sodium tetraphenylborate under mild visible light photoredox conditions. This verified by cross-electrophile coupling and carbon dioxide synthesis carboxylic acids. Direct transformation a range primary, secondary, tertiary benzyl to acids achieved. Control experiments computational studies indicate that undergoes homolysis bond, generating alkyl radicals. After reducing into anion conditions, following carboxylation CO2 affords product.

Language: Английский

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Recent advancements in the use of Bobbitt's salt and 4-acetamidoTEMPO

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(95), P. 14063 - 14092

Published: Jan. 1, 2023

This feature article provides a comprehensive overview of recent developments and applications Bobbitt's salt 4-acetamidoTEMPO in organic synthesis fields beyond.

Language: Английский

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Formation of C–B, C–C, and C–X Bonds from Nonstabilized Aryl Radicals Generated from Diaryl Boryl Radicals

ACS Central Science, Journal Year: 2023, Volume and Issue: 9(12), P. 2268 - 2276

Published: Nov. 13, 2023

With the development of organoboron chemistry, boron-centered radicals have become increasingly attractive. However, their synthetic applications remain limited in that they been used only as substrates for addition reactions or initiators catalytic reactions. We achieved a new reaction pathway which tetraarylborate salts are precursors aryl via boron radicals, by introducing simple activation reagent. In addition, we carried out diverse array transformations involving these radical precursors, allowed construction C–B, C–C, and C–X bonds presence visible light.

Language: Английский

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Modular assembly of versatile tetrasubstituted alkenyl monohalides from alkynyl tetracoordinate borons

Chem, Journal Year: 2023, Volume and Issue: 9(5), P. 1164 - 1181

Published: Feb. 6, 2023

Language: Английский

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Deboronative functionalization of alkylboron species via a radical-transfer strategy

Chemical Science, Journal Year: 2024, Volume and Issue: 15(35), P. 14241 - 14247

Published: Jan. 1, 2024

We describe a method for activating C–B bonds by nitrogen- or oxygen-radical transfer that is applicable to alkylboronic acids and esters.

Language: Английский

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Transition‐Metal‐Free Oxidative Cross‐Coupling of Tetraarylborates to Biaryls Using Organic Oxidants

Angewandte Chemie International Edition, Journal Year: 2020, Volume and Issue: 59(36), P. 15468 - 15473

Published: March 11, 2020

Abstract Readily prepared tetraarylborates undergo selective (cross)‐coupling through oxidation with Bobbitt's salt to give symmetric and unsymmetric biaryls. The organic oxoammonium can be used either as a stoichiometric oxidant or catalyst in combination situ generated NO 2 molecular oxygen the terminal oxidant. For selected cases, oxidative coupling is also possible /O without any additional nitroxide‐based cocatalyst. Transition‐metal‐free catalytic ligand cross‐coupling of unprecedented introduced method provides access various biaryl heterobiaryl systems.

Language: Английский

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Asymmetric Electrochemical Arylation in the Formal Synthesis of (+)-Amurensinine

CCS Chemistry, Journal Year: 2021, Volume and Issue: 3(12), P. 338 - 347

Published: Jan. 9, 2021

Open AccessCCS ChemistryCOMMUNICATION1 Dec 2021Asymmetric Electrochemical Arylation in the Formal Synthesis of (+)-Amurensinine Qinglin Zhang, Kang Liang and Chang Guo Zhang Hefei National Laboratory for Physical Sciences at Microscale, Department Chemistry, University Science Technology China, 230026 Google Scholar More articles by this author , *Corresponding author: E-mail Address: [email protected] https://doi.org/10.31635/ccschem.021.202000720 SectionsSupplemental MaterialAboutAbstractPDF ToolsAdd to favoritesDownload CitationsTrack Citations ShareFacebookTwitterLinked InEmail Asymmetric electrochemical synthesis has emerged as an attractive sustainable alternative distinctive activation bond connections preparation diverse enantiomerically enriched targets, including natural products pharmaceutical agents. Herein, we describe chiral Lewis acid-catalyzed enantioselective anodic coupling reaction a key step presented formal isopavine alkaloids. The direct functionalization catechol derivatives with 2-acyl imidazoles was developed provide wide range useful α,α-diaryl carbonyl building blocks containing tertiary stereogenic centers high reactivity excellent stereoselectivity. utility novel protocol is showcased its implementation (+)-Amurensinine. Download figure PowerPoint Introduction advances made asymmetric catalytic forge new carbon–carbon bonds levels stereoselectivity have provided access molecular scaffolds that are ubiquitous organic functional materials, pharmaceuticals, products.1 Isopavine alkaloids2–5 represent family alkaloids commonly been isolated from widespread series sources, exhibiting remarkable biological properties (Figure 1a).6 From synthetic standpoint, enolate arylation would simple straightforward approach generate structural motifs I carbon stereoselective manner.7–10 However, racemization via enolization process associated architecture 1b).11,12 In context, sought develop complementary strategy allow construction architectural elements found (+)-Amurensinine.13–15 Figure 1 | Design synthesis. (a) Representative biologically relevant compounds. (b) carbonyls. (c) Enantioselective leading total isopavin alkaloid. enabling platform mild efficient bond-forming reactions without requirement stoichiometric quantities chemical oxidants or reductants.16–31 feasibility demonstrated providing rapid multiple product selectively.32–35 transformation36–38 assembly unique core combination installation requisite carbonyl-containing groups pursue bioactive molecules presents significant challenges.39–45 Given pharmacological importance alkaloids, electrolysis46–57 enantiopure analogs context highly desirable. Recently, Meggers group58 our group59 established α-functionalization compounds enabled acid catalysis constructions. discovery protocols remains formidable challenge, thus offering opportunity targeted enables stereocenter stereocontrol demonstrates potential application achiral precursors 1c). Experimental Methods available Supporting Information. Results Discussion Optimization studies Our initially evaluated using imidazole 1a tert -Butyldimethylsilyl (TBS)-protected 2a substrates along nickel catalysts analog (Table 1). Indeed, use diamine 4a ligand led desired adduct 3a moderate yield, but poor enantioselectivity undivided cell under galvanostatic conditions (entry 1, 49% 7% ee). Next, different types ligands determine their influence on transformation (entries 1–6). Gratifyingly, could be forged 83% yield 93% ee when 4d bulky 2,4,6-trichloro-phenyl group employed 4). No improvement observed varying base temperature 7–10). copper allowed albeit 11). Remarkably, control experiments verified necessity each component 12–15). absence ligand, no formed 12–14). As expected, occurred externally applied electric current 15). Notably, only 12% NaIO4 oxidant 16). Further exploration revealed slightly decreased Pt electrodes 17). Table Reaction Conditions Entry Acid 4 Base Yield (%) Ni(OAc)2 Quinuclidine 49 7 2 4b 44 47 3 4c 54 92 83 93 5 4e 82 84 6 4f 90 40 DIPEA 67 77 8a 2,6-Lutidine 31 9b 51 10c 36 91 11 Cu(OAc)2 52 13 12 — NR 14 15d 16e 17f 60 Note: Reactions were carried out substrate (0.1 mmol, 1.0 equiv), (0.15 1.5 (10 mol %), (20 nBu4NPF6 (0.3 3.0 equiv) Dichloromethane (DCM) (4 mL) −40 °C 24 h. DIPEA, N,N-diisopropylethylamine; NR, reaction. aWith 10 % base. bAt 0 °C. cAt −78 °C, 48 dWithout current. eNaIO4 (1.5 electricity. fWith electrodes. Synthetic present highlighted applying it according following sequence 2). crucial bearing disubstituted phenyl 1b accomplished catalyst conditions, forming corresponding 3b 92% 85% ee. dimethylation (trimethylsilyl)diazomethane (TMSCHN2) furnished 86% any loss enantiomeric excess. Initial attempts conduct methylation utilizing known methods cleavage failed various conditions. A detailed description these functionality effectively transformed into ester upon treatment trimethyloxonium tetrafluoroborate (Me3O · BF4) reagent followed addition methanol Diazabicyclo[5.4.0]undec Diazabicyclo[5.4.0]undec-7-ene (DBU) one-pot operation.60 Reduction presence LiAlH4, O-triisopropylsilyl (O-TIPS) protection further removal TBS moiety, finally afforded alcohol 9. subsequent oxidation cyclization carbocyclic structure good yield. Carbonyl reduction l-selectride generated 12, which can converted Stoltz’s procedures.13 Furthermore, spectroscopy optical rotation agreement data previously reported literature.13 Scope TBS-protected probe scope optimal 3). variety investigated optimized electronic nature substituents para positions benzene ring seemed obvious ( 3c– 3j); however, yields varied remarkably some cases 3h– 3j). meta ortho aryl moiety had negligible impact 3k–3n). Generally, enantioselectivities attained group, heterocyclic 3o 3p). N-phenyl-substituent (R2) slight negative 3q). Substrate imidazoles. (40 %). generality concerning partners also 4a). Modified alkyl substrates, such protected oxygen chloride, 3r 3s). electron-deficient position underwent smooth arylations 3t 3u). addition, 4-methylcatechol suitable target 3v 81% 94% Pleasingly, broad differently ortho-substituted proved 3w–3y). method compatible pyrocatechol, giving 3z great enantioselectivity. 2-aminophenol undergo reaction, indicating backbone succeed. Following derivatization, absolute stereochemistry determined X-ray crystallography derivatization 4b). It consistent configuration catechols. component. crystallography. equiv).bWith constant 0.8 mA. cIn quinuclidine. Mechanistic To understand mechanistic details reactions, initiated study conducting cyclic voltammetry (CV) redox components. shown 5a, two peaks 1.40 2.28 V versus saturated calomel electrode (SCE) MeCN Information S2). first anode dropped (vs SCE) derivative 0.34 quinuclidine facilitate proton-coupled electron transfer (PCET) 5b Figures S4 S5), elucidating pathways originate generation para-phenoxyl radical intermediate61–67 oxidative [Ni( 4d)] 2.08 1.87 SCE MeCN) S1 S3). Similarly, CV bound- 4d)- 1a] shifted significantly lower 5c, E = 0.58 vs S6 S7) suggested existence 1a]· intermediate diradical behavior process. response increased increasing concentrations 5d S8). confirm assumption, controlled electrolysis 5e) 0.50 gave comparable results instead entry 9), suggesting 1,2-benzoquinone (Ep/2 2.11 contributed minimally reactivity. Besides, standard electrolytic condition 2,2,6,6-Tetramethylpiperidinooxy (TEMPO) TEMPO-trapping 6% 5f). us propose might active species (see details). investigation coupling. related solvent 0.1 M nBu4NPF6. [Ni(4d)-1a] (d) relationship quinuclidine, (1) catalyst; (2) [Ni(4d)]; (3) 20 (4) 30 (5) [Ni(4d)]. (e) Potential-controlled between 2a. (f) Experiments trap Lewis-acid-bound species. Based experiments, plausible cycle outlined 6. coordination 1,68–72 formation III electrolysis-induced single (SET) oxidation. parallel cycle, promotes IV 2. Subsequently, radical–radical proposed afford final 3. Proposed mechanism. Conclusion We cross-coupling derivatives, expeditious multifunctionalized stereocenter. This features enantioselectivity, yields, functional-group tolerance, making applicable structurally complex compounds, drug discovery. Significantly, unified methodology preliminarily explored Supplemental includes experimental procedures compound characterization data. 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Previous articleNext article FiguresReferencesRelatedDetailsCited ByLiu S, Zhao W, J, N, C, X, Y, Y Cheng X (2021) Aziridination Tetrasubstituted Alkenes Ammonia, CCS 4:2, (693-703), Online publication date: 1-Feb-2022.Cheng A, T, H, K C (2022) Synthesis, 4:4, (1120-1152), 1-Apr-2022. Issue AssignmentVolume 3Issue 12Page: 338-347Supporting Copyright & Permissions© 2021 Chinese Chemical SocietyKeywordselectrochemistryarylationLewis catalysisasymmetric catalysisαα-diaryl skeletons Downloaded 1,551 times PDF DownloadLoading ...

Language: Английский

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Hydroalkylation of styrenes enabled by boryl radical mediated halogen atom transfer

Chemical Science, Journal Year: 2024, Volume and Issue: 15(23), P. 8813 - 8819

Published: Jan. 1, 2024

NaBPh 4 was employed in a Halogen Atom Transfer methodology to generate C-centered radicals from alkyl and aryl bromides iodides.

Language: Английский

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