Synfacts

Issue 10 · October 2020

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SYNFORM ISSUE 2020/10
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Synthesis of (±)-Cryptotrione
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Asymmetric Synthsis of (S)-Verapamil

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Synthesis of 4-(Aminomethyl)quinolin-2(1H)-ones
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Formal Synthesis of (±)-Haouamine A

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Synthesis of β-Lactamase Inhibitor QPX7728

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Total Synthesis of (+)-Tagetitoxin

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Synthesis of (+)-Rubellin C

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Synthesis of a Glucokinase Activator

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Synthesis of β-Lactamase Inhibitor IID572

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Total Synthesis of Bufospirostenin A

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Total Synthesis of (–)-Arborisidine

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Synthesis of BMS-986260

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Synthesis of AB928

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Synthesis of (±)-Hibiscone C
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Synthesis of Heterocycles
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Modular Syntheses of 5- and 6-Azaindoles

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1148
Modular Synthesis of 2,5-Diaryltetrazoles

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1149
Synthesis of C2-Substituted Imidazolones

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1150
Nickel-Catalyzed Enantioselective Synthesis of 3,3-Disubstituted Oxindoles

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1151
Cine-Substitutions of Five-Membered Hetarenes via Sulfonium Salts

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1152
Synthesis of Indoles through C–C and C–N Bond Formation of Aliphatic Amines and Nitrosoarenes

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1153
One-Pot Synthesis of Polycyclic Indolones by Photocatalytic Annulation of Redox-Active Esters

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1154
Bismuth(III)-Catalyzed Synthesis of 2-(Fluoroalkyl)imidazole-5-carbaldehydes

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1155
A Sequential C–H Activation–Annulation Route to Fused Phthalimides

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1156
Copper-Catalyzed Three-Component Synthesis of γ-Lactams

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1157
Synthesis of Chiral γ-Lactams through Pd(II)-Catalyzed Cascade Alkenylation/Aza-Wacker Cyclization

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1158
Indium-Catalyzed Synthesis of 1,2-Dihydroquinolines through Rearrangement of Oxetanes

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Synthesis of Materials and Unnatural Products
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1159
So Long, Sulfur!

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1160
About to Take Off? A Flapping Peryleneimide Fluorophore with Tunable Fluorogenic Properties

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1161
Handedness Lends a Hand: Chirality-Assisted Synthesis of Enantioenriched Triptycene Derivatives

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1162
Two Reaction Conditions, One New Pentacyclic Pyrylium Emitter

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1163
Multitasking Material: A Porous 3D Organic Polymer with High Surface-Area and Semiconducting Properties

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1164
But Wait, There’s More to Cyclo[18]carbon!

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1165
Expanding the Circulene Family

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1166
Belt-Like Macrocycles as Molecular Containers

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1167
Two New Phenalenannulation Designs

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1168
A New Path to 9,10-Dihydroacridines and Nitrogen-Doped Polyacenes

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1169
Bright Boron Binders: Highly Fluorescent Acylated ‘BDan’ Compounds

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1170
All Nitriles Lead to Imidazoles

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Metals in Synthesis
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Rhodium-Catalyzed Enantioselective Diarylcarbene Insertion into Si–H Bonds
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1172
Radical Relayed Reductive Coupling for Double Functionalization of Vinylamides and -boranes

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1173
Palladium-Catalyzed Cross-Couplings of Alkyllithiums with Aryl Chlorides
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1174
Hydroamination of Styrenes under Air and Moisture

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1175
Copper-Catalyzed C_sp–S Couplings

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1176
Nickel-Catalyzed Asymmetric Synthesis of Methylenecyclopropanes

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1177
Enantioselective Hydroxylation of Benzylic C(sp³)–H Bonds Catalyzed by a Chiral Aryl Iodide and Copper

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1178
Synthesis of Bicyclic Lactones by Palladium-Catalyzed Carbonylative Cyclopropanol Ring-Opening

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1179
Iron-Catalyzed Three-Component Difunctionalization of Unactivated Alkenes

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1180
Dual NHC/Photoredox Catalysis for the Synthesis of β-CF₃ (Hetero)Aryl Ketones

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1181
Palladium-Catalyzed Enantioselective Aminoazidation Reaction of Unactivated Alkenes

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1182
Tandem Trifluoromethylation and Cyanation/Etherification of Vinylamides and -esters

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1183
Benzylic C–H Functionalization via Copper-Catalyzed Fluorination

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1184
Enantioselective Coupling of Allylic Carbonates with Vinyl Azides by Iridium Catalysis

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1185
Atroposelective Ring Opening of Cyclic Diaryliodonium Salts Using a Chiral Co Anion and Cu Catalyst

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1186
Palladium-Catalyzed Dialkylation of Aromatics

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1187
Alkenylation of Olefins with β-Nitrostyrenes

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1188
Cobalt-Catalyzed Enantioselective Radical Cyclization of Alkenyl Alcohols

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1189
Spiroaminals and Fused Bicycles via an Enantioselective Cyclopropanation–Rearrangement Protocol

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1190
α-Arylation of Acetone using Aryl Chlorides and Nickel Catalysis

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1191
Rhodium-Catalyzed Stereospecific Cyanomethylation of Tertiary Allylic Carbonates

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1192
Hydroalumination of Allenes via Copper Catalysis for the Synthesis of β,γ-Unsaturated Ketones

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1193
Carbonylative C(sp³)–H Activation for Synthesis of Amides and Esters

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1194
Cleavage of C–O Bond in α-Alkoxy Ketones via Cobalt Catalysis

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1195
Copper-Catalyzed Enantioselective Hydroacylation Reaction of Allenes

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1196
Copper-Catalyzed ortho-Functionalization of Naphthols and Phenols

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1197
Synthesis of Enantioenriched Isobenzofuranones via Bismuth and Phosphoric Acid Catalyzed Allylation

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1198
Preparation of Functionalized 3-Arylpropanamides

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1199
Corey–Fuchs Alkyne Synthesis
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1200
ortho-Functionalization of Quinoline N-Oxides under Copper Catalysis

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Polymer-Supported Synthesis
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Hydrogenation of Alkynes to Alkenes on Pd NPs Supported on Cubic Cu in a Metal–Organic Framework

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1202
Silylation of Aryl Chlorides on Palladium–Gold Alloy Nanoparticles Supported on Zirconia

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Anti-Markovnikov Regioselective Hydroamination of Alkenes with Aqueous NH₃on a Au/TiO₂Photocatalyst
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1204
Iridium-Catalyzed Acceptorless Dehydrogenation of N-Heterocycles and Hydrogenation of N-Hetarenes

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1205
Reduction of Carbonyl Compounds by Diethylsilane Catalyzed by Titania-Supported Gold Nanoparticles

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1206
Carbon Nanotube Supported Ni/Pd-Nanoparticles on for Carbonylative Suzuki–Miyaura Coupling

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1207
Aerobic Oxidation of Vanillic Alcohol with Pd/C and Sn-Pd/C

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1208
Hydrogenation of Nitriles Catalyzed by Cobalt Phosphide Supported on Hydrotalcite

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1209
Asymmetric Strecker Reaction Catalyzed by a Copper Porphyrin-Based Covalent Organic Framework

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1210
Synthesis of N-Alkoxymethylated Benzimidazoles on Indium Oxide Nanoparticles

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Organo- and Biocatalysis
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1211
Tetrapeptide-Catalyzed Dynamic Kinetic Resolution Grants Access to Helically Chiral Loratadine Analogues
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1212
Confined N-Hydroxyimide-Catalyzed Site-Selective Radical Benzylic Amination

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1213
A Catalytic Birch Reduction through a Consecutive Photoinduced Electron-Transfer Process

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1214
Chiral Amine-Boronic Acid Catalysis: Enantioselective 1,4-Addition to α,β-Unsaturated Carboxylic Acids

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1215
C₄-Selective Alkylation of Pyridinium Salts Driven by Photoactivity of an Electron Donor–Acceptor Complex

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1216
Highly Enantioselective and Stereodivergent Synthesis of Cyclopropyl δ-Lactones

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1217
Quinacridinium Ion as a Versatile Organic Photoredox Catalyst for Red-Light-Mediated Reactions

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1218
Enantioselective Synthesis of α-Amino Ketones by Asymmetric Counteranion-Directed Catalysis

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1219
A New Catalytic Radical-Based α-Deoxygenation of Benzoin Derivatives

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1220
Organophotocatalytic Boron-Mediated Geometric Isomerization of Alkenes

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Chemistry in Medicine and Biology
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1221
A Long-Lasting HIV-Capsid Inhibitor

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1222
Orexin-1-Receptor-Selective Antagonists through Structure-Based Drug Design

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1223
Peptide Antagonist of CGRP Receptor for Migraine Treatment

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1224
Light-Controlled Carbonation

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1225
6-Aza-artemisinins as Potent Antimalarial Drugs

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1226
Depalmitoylation Strategy to Inhibit NRAS Signaling

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1227
Hapten Deuteration of a Heroin Vaccine

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1228
Structural Modification of Oridonin Yields A More Potent Anticancer Agent

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1229
Total Synthesis of N¹⁴-Desacetoxytubulysin H Using Passerini Multicomponent Reaction (MCR)

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1230
Janelia Fluor Photosensitizers

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1231
Covalent Inhibitors for PIP Signaling

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1232
Maleimides Allow for Cycloaromatization of Acyclic Enediynes

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1233
Efficient Total Synthesis of Lipid I and Lipid II Analogues

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1234
SYK Inhibitor with Improved hERG-Profile

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1235
Dansyl’s First Dance
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Peptide Chemistry
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1237
Coupling of Amino Acids and α-Branched Aldehydes
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1238
Vicinal Tetrasubstituted Oxindole-Derived Acyclic Amino Acid Synthesis by a Mannich-Type Reaction

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1239
One-Pot Synthesis of β-Amino Secondary Amides from Vinylic Azides and N-Acyl Imines

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1240
Efficient Method for Peptide Synthesis in Water by Using Amphiphile PS-750-M

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1241
Metallaphotoredox-Catalyzed Synthesis of γ-Amino Acid Derivatives

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1242
[3+2]-Cycloaddition Reaction for the Synthesis of Spirocyclic α-Amino Esters

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1243
Cu-Catalyzed Ligand-Controlled Synthesis of β-Amino Acid Derivatives

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1244
Synthesis of Fluorinated Quaternary α-Amino Acid Esters

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1245
Photoredox Decarboxylative Coupling for α-Amino Acids Synthesis

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1246
Copper-Catalyzed C(sp³)–H Bond Activation to Access α-Alkoxylated Amino Amide Derivatives

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1247
Synthesis of Reactive Amino Acid Esters by Using 9-Fluorenylmethyl Chloroformate
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Flow Chemistry
z1249
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1249
Selective Monoreduction of a Pyridine Diester on a Kilogram Scale

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1250
Development of an Efficient Flow Hydroformylation in a High-Throughput Single-Droplet Reactor

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1251
Scalable Electrochemical Cyclobutane Synthesis in Continuous Flow

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1252
Photocatalytic Carbonylative Amidation in Continuous Flow

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1253
Polymer-Supported Tin-Catalyzed Synthesis of Tetrazoles in Flow

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1254
Synthesis of Heteroaryl Sulfinates in Continuous Flow for Use in Palladium-Catalyzed Cross-Coupling

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1255
Aryl Amine Synthesis in an Integrated Packed-Bed Flow System

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