Rhodium‐Complex‐Catalyzed Hydroformylation of Olefins with CO2 and Hydrosilane

Rhodium‐Complex‐Catalyzed Hydroformylation of Olefins with CO2 and Hydrosilane: A rhodium‐catalyzed one‐pot hydroformylation of olefins with CO2 , hydrosilane, and H2 has been developed that affords the aldehydes in good chemoselectivities at low catalyst loading. Mechanistic studies...

Highly ortho‐Selective Chlorination of Anilines Using a Secondary Ammonium Salt Organocatalyst

Highly ortho‐Selective Chlorination of Anilines Using a Secondary Ammonium Salt Organocatalyst: An organocatalytic, highly facile, efficient, and regioselective ortho‐chlorination of anilines is described. A secondary ammonium chloride salt has been employed as the catalyst and the reaction can be...

Organocatalytic Friedel–Crafts Alkylation/Lactonization Reaction of Naphthols with 3‐Trifluoroethylidene Oxindoles: The Asymmetric Synthesis of Dihydrocoumarins

Organocatalytic Friedel–Crafts Alkylation/Lactonization Reaction of Naphthols with 3‐Trifluoroethylidene Oxindoles: The Asymmetric Synthesis of Dihydrocoumarins: Naphthols and 3‐trifluoroethylidene oxindoles were found to undergo an asymmetric Friedel–Crafts alkylation/lactonization reaction, catalyzed by only 2.5 mol % of a quinine‐derived squaramide catalyst,...

Stapled Peptides by Late‐Stage C(sp3)−H Activation

Stapled Peptides by Late‐Stage C(sp3)−H Activation: Despite the importance of stapled peptides for drug discovery, only few practical processes to prepare cross‐linked peptides have been described; thus the structural diversity of available staple motifs...

Enyne [4 4] Cycloaddition/Oxidation: Ring Contraction via Cyclopropanones and Their Anionic Ring‐Opening Reactions

Enyne [4 4] Cycloaddition/Oxidation: Ring Contraction via Cyclopropanones and Their Anionic Ring‐Opening Reactions: Irradiation of a 1,3‐enyne tethered to a 2‐pyridone, in the presence of oxygen, leads to formation of a seven‐membered ring product, an overall [4+4−1] reaction. This transformation involves two unstable...

Cerium‐Catalyzed Hydrosilylation of Acrylates to Give α‐Silyl Esters

Cerium‐Catalyzed Hydrosilylation of Acrylates to Give α‐Silyl Esters: The homoleptic organocerium complex Ce{C(SiHMe2)3}3 (1) reacts with B(C6F5)3 to produce the zwitterionic bis(alkyl) hydridoborato Ce{C(SiHMe2)3}2HB(C6F5)3 (2). NMR and IR spectroscopy and X‐ray crystallography...

Regio‐ and Enantioselective Cobalt‐Catalyzed Sequential Hydrosilylation/Hydrogenation of Terminal Alkynes

Regio‐ and Enantioselective Cobalt‐Catalyzed Sequential Hydrosilylation/Hydrogenation of Terminal Alkynes: A highly regio‐ and enantioselective cobalt‐catalyzed sequential hydrosilylation/hydrogenation of alkynes was developed to afford chiral silanes. This one‐pot method is operationally simple and atom economic....

Copper‐Catalyzed Bromination of C(sp3)−H Bonds Distal to Functional Groups

Copper‐Catalyzed Bromination of C(sp3)−H Bonds Distal to Functional Groups: Selective bromination of γ‐methylene C(sp3)−H bonds of aliphatic amides and δ‐methylene C(sp3)−H bonds of nosyl‐protected alkyl amines are developed using NBS as the brominating reagent and catalytic amount...

BCl3‐Induced Annulative Oxo‐ and Thioboration for the Formation of C3‐Borylated Benzofurans and Benzothiophenes

BCl3‐Induced Annulative Oxo‐ and Thioboration for the Formation of C3‐Borylated Benzofurans and Benzothiophenes: BCl3‐induced borylative cyclization of aryl‐alkynes possessing ortho‐EMe (E=S, O) groups represents a simple, metal‐free method for the formation of C3‐borylated benzothiophenes and benzofurans. The dichloro(heteroaryl)borane...

An Expedient Total Synthesis of Chivosazole F: an Actin‐Binding Antimitotic Macrolide from the Myxobacterium Sorangium Cellulosum

An Expedient Total Synthesis of Chivosazole F: an Actin‐Binding Antimitotic Macrolide from the Myxobacterium Sorangium Cellulosum: A unified strategy for the chemical synthesis of the chivosazoles is described. This strategy is based on two closely related approaches involving the late‐stage installation of the isomerization‐prone...

Review: Electrophilic Aromatic Substitution with Silicon Electrophiles: Catalytic Friedel–Crafts C−H Silylation - Bähr - 2016 - Angewandte Chemie International Edition - Wiley Online Library

Electrophilic Aromatic Substitution with Silicon Electrophiles: Catalytic Friedel–Crafts C−H Silylation - Bähr - 2016 - Angewandte Chemie International Edition - Wiley Online Library: Electrophilic aromatic substitution is a fundamental reaction in synthetic chemistry. It converts C−H bonds of sufficiently nucleophilic arenes into C−X and C−C bonds using either stoichiometrically added...

Exploiting Deep Eutectic Solvents and Organolithium Reagent Partnerships: Chemoselective Ultrafast Addition to Imines and Quinolines Under Aerobic Ambient Temperature Conditions - Vidal - 2016 - Angewandte Chemie International Edition - Wiley Online Library

Exploiting Deep Eutectic Solvents and Organolithium Reagent Partnerships: Chemoselective Ultrafast Addition to Imines and Quinolines Under Aerobic Ambient Temperature Conditions - Vidal - 2016 - Angewandte Chemie International Edition - Wiley Online Library:
Shattering the long‐held dogma that organolithium chemistry needs to be performed under inert atmospheres in toxic organic solvents, chemoselective addition of organolithium reagents to non‐activated imines...

Iridium-Catalyzed Stereoselective Allylic Alkylation Reactions with Crotyl Chloride - Hethcox - 2016 - Angewandte Chemie International Edition - Wiley Online Library

Iridium-Catalyzed Stereoselective Allylic Alkylation Reactions with Crotyl Chloride - Hethcox - 2016 - Angewandte Chemie International Edition - Wiley Online Library:
The development of the first enantio‐, diastereo‐, and regioselective iridium‐catalyzed allylic alkylation reaction of prochiral enolates to form an all‐carbon quaternary stereogenic center with an aliphatic‐substituted...

Enantioselective (4 2) Annulation of Donor–Acceptor Cyclobutanes by N-Heterocyclic Carbene Catalysis - Levens - 2016 - Angewandte Chemie International Edition - Wiley Online Library

Enantioselective (4 2) Annulation of Donor–Acceptor Cyclobutanes by N-Heterocyclic Carbene Catalysis - Levens - 2016 - Angewandte Chemie International Edition - Wiley Online Library:
 Herein we report the enantioselective (4+2) annulation of donor–acceptor cyclobutanes and unsaturated acyl fluorides using N‐heterocyclic carbene catalysis. The reaction allows a 3‐step synthesis of cyclohexyl...

Strategic Utilization of Multifunctional Carbene for Direct Synthesis of Carboxylic–Phosphinic Mixed Anhydride from CO2 - Hoshimoto - 2016 - Angewandte Chemie International Edition - Wiley Online Library

Strategic Utilization of Multifunctional Carbene for Direct Synthesis of Carboxylic–Phosphinic Mixed Anhydride from CO2 - Hoshimoto - 2016 - Angewandte Chemie International Edition - Wiley Online Library:
Direct synthesis of carboxylic–phosphinic mixed anhydrides has been achieved by treating carbon dioxide with N‐phosphine oxide‐substituted imidazolylidenes (PoxIms) that contain both nucleophilic carbene...

Superacid-Catalyzed Trifluoromethylthiolation of Aromatic Amines - Bonazaba Milandou - 2016 - Angewandte Chemie International Edition - Wiley Online Library

Superacid-Catalyzed Trifluoromethylthiolation of Aromatic Amines - Bonazaba Milandou - 2016 - Angewandte Chemie International Edition - Wiley Online Library: Upon activation under superacid conditions, functionalized tailor‐made N‐SCF3 sulfenamides served as reagents for the trifluoromethylthiolation of aromatic amines. This method has a broad substrate scope...

Transaminase Triggered Aza-Michael Approach for the Enantioselective Synthesis of Piperidine Scaffolds - Journal of the American Chemical Society (ACS Publications)

Catalytic activation of carbon-carbon bonds in cyclopentanones

  • Catalytic activation of carbon–carbon bonds in cyclopentanones
    Ying Xia, Gang Lu, Peng Liu & Guangbin Dong
    Nature 539, 546–550 doi:10.1038/nature19849

    In the chemical industry, it is often necessary to activate carbon–carbon bonds in order to synthesize complex organic molecules, but this is challenging when starting with simple five- or six-membered carbon rings; a new method uses a rhodium pre-catalyst and an amino-pyridine co-catalyst, enabling an overall energetically favourable reaction that involves activation of carbon–carbon bonds plus activation of carbon–hydrogen bonds.
     

A Thieno[3,4-b]thiophene-Based Non-fullerene Electron Acceptor for High-Performance Bulk-Heterojunction Organic Solar Cells - Journal of the American Chemical Society (ACS Publications)

Visible Light-Gated Cobalt Catalysis for a Spatially and Temporally Resolved [2 2 2] Cycloaddition - Journal of the American Chemical Society (ACS Publications)

Total Syntheses of Aflavazole and 14-Hydroxyaflavinine - Journal of the American Chemical Society (ACS Publications)

Metal-Free Enantioselective Oxidative Arylation of Alkenes: Hypervalent-Iodine-Promoted Oxidative C−C Bond Formation - Shimogaki - 2016 - Angewandte Chemie International Edition - Wiley Online Library

Arenophile-Mediated Dearomative Reduction - Okumura - 2016 - Angewandte Chemie International Edition - Wiley Online Library

Stereoselective Carbonyl Olefination with Fluorosulfoximines: Facile Access to Z or E Terminal Monofluoroalkenes - Liu - 2016 - Angewandte Chemie International Edition - Wiley Online Library

Combining Organocatalysis and Lanthanide Catalysis: A Sequential One-Pot Quadruple Reaction Sequence/Hetero-Diels–Alder Asymmetric Synthesis of Functionalized Tricycles - Dochain - 2016 - Angewandte Chemie International Edition - Wiley Online Library

Catalytic Asymmetric Reductive Condensation of N–H Imines: Synthesis of C2-Symmetric Secondary Amines - Wakchaure - 2016 - Angewandte Chemie International Edition - Wiley Online Library

Simple Copper Catalysts for the Aerobic Oxidation of Amines: Selectivity Control by the Counterion - Xu - 2016 - Angewandte Chemie International Edition - Wiley Online Library

N-Heterocyclic Carbene Catalyzed γ-Dihalomethylenation of Enals by Single-Electron Transfer - Yang - 2016 - Angewandte Chemie International Edition - Wiley Online Library

Enantioselective Copper-Catalyzed Intermolecular Cyanotrifluoromethylation of Alkenes via Radical Process - Journal of the American Chemical Society (ACS Publications)

Enantioselective Rhodium-Catalyzed Allylic Alkylation of Prochiral α,α-Disubstituted Aldehyde Enolates for the Construction of Acyclic Quaternary Stereogenic Centers - Journal of the American Chemical Society (ACS Publications)

Contra-thermodynamic Hydrogen Atom Abstraction in the Selective C–H Functionalization of Trialkylamine N-CH3 Groups - Journal of the American Chemical Society (ACS Publications)

Sequential C–H Arylation and Enantioselective Hydrogenation Enables Ideal Asymmetric Entry to the Indenopiperidine Core of an 11β-HSD-1 Inhibitor - Journal of the American Chemical Society (ACS Publications)

Eight-Step Enantioselective Total Synthesis of (−)-Cycloclavine - McCabe - 2016 - Angewandte Chemie International Edition - Wiley Online Library

Asymmetric synthesis of batrachotoxin: Enantiomeric toxins show functional divergence against NaV

A general catalytic β-C–H carbonylation of aliphatic amines to β-lactams

PhSO2SCF2H: A Shelf-Stable, Easily Scalable Reagent for Radical Difluoromethylthiolation - Zhu - 2016 - Angewandte Chemie International Edition - Wiley Online Library

Synthesis of Atisine, Ajaconine, Denudatine, and Hetidine Diterpenoid Alkaloids by a Bioinspired Approach - Li - 2016 - Angewandte Chemie International Edition - Wiley Online Library

Assembly of Terpenoid Cores by a Simple, Tunable Strategy - Lahtigui - 2016 - Angewandte Chemie International Edition - Wiley Online Library

Palladium-Catalyzed Fluorination of Cyclic Vinyl Triflates: Effect of TESCF3 as an Additive - Ye - 2016 - Angewandte Chemie International Edition - Wiley Online Library

Practical Photocatalytic Trifluoromethylation and Hydrotrifluoromethylation of Styrenes in Batch and Flow - Straathof - 2016 - Angewandte Chemie International Edition - Wiley Online Library

Efficient Coupling Reaction of Quinone Monoacetal with Phenols Leading to Phenol Biaryls - Kamitanaka - 2016 - Angewandte Chemie International Edition - Wiley Online Library

Rhodium(III)-Catalyzed Alkenylation–Annulation of closo-Dodecaborate Anions through Double B−H Activation at Room Temperature - Zhang - 2016 - Angewandte Chemie International Edition - Wiley Online Library

Rhodium-Catalyzed Diastereoselective Cyclization of Allenyl-Sulfonylcarbamates: A Stereodivergent Approach to 1,3-Aminoalcohol Derivatives - Spreider - 2016 - Angewandte Chemie International Edition - Wiley Online Library

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