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C–C Coupling

The development of metal-catalyzed cross-coupling reactions over the past 30 years has revolutionized the way, carbon-carbon bonds between sp and sp2 carbon atoms are formed. These methods have profoundly changed the protocols for the construction of natural products, building blocks for supramolecular chemistry and self-assembly, organic materials and polymers, and lead compounds in medicinal chemistry from simpler entities. The 2010 Nobel prize in chemistry for E. Negishi, R. Heck, and A. Suzuki underlines the importance of direct bond formation betweeen carbon atoms.

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Model Macrocyclic Ligands for Proof-of-Concept Mechanistic Studies in Transition-Metal Catalysis

Model Macrocyclic Ligands for Proof‐of‐Concept Mechanistic Studies in Transition‐Metal Catalysis

How does it work? The design of model macrocyclic substrate platforms to unravel mechanistic details at a molecular level of C−C or C−heteroatom bond-forming processes catalyzed by transition metals are highlighted.

[Concept]
Xavi Ribas, Marc Devillard
Chem. Eur. J., December 12, 2017, https://doi.org/10.1002/chem.201704408 Read article

Macrolide Synthesis through Intramolecular Oxidative Cross-Coupling of Alkenes

Macrolide Synthesis through Intramolecular Oxidative Cross‐Coupling of Alkenes

Two pair: A RhIII-catalyzed intramolecular oxidative cross-coupling between double bonds for the synthesis of macrolides is described. Under the optimized conditions, macrocycles containing a diene moiety can be formed in reasonable yields and with excellent chemo- and stereoselectivity. This provides efficient access to macrocyclic compounds containing 1,3-conjugated dienes.

[Communication]
Bing Jiang, Meng Zhao, Shu-Sen Li, Yun-He Xu, Teck-Peng Loh
Angew. Chem. Int. Ed., December 12, 2017, https://doi.org/10.1002/anie.201710601 Read article

Efficient Microwave-Assisted Synthesis of Sonogashira-Coupled Perylene Monoimide Derivatives: Impact of Electron-Donating Groups on Optoelectronic Properties

Efficient Microwave‐Assisted Synthesis of Sonogashira‐Coupled Perylene Monoimide Derivatives: Impact of Electron‐Donating Groups on Optoelectronic Properties

Faster than conventional coupling: A simple microwave-assisted protocol for the synthesis of a series of peri-coupled perylene monoimide derivatives by Sonogashira coupling is reported. This method is significantly faster than the conventional coupling method and provides products with interesting optoelectronic properties in moderate to good yields.

[Communication]
Vikas Sharma, Falguni Chandra, Dhananjaya Sahoo, Apurba L. Koner
Eur. J. Org. Chem., December 08, 2017, https://doi.org/10.1002/ejoc.201701310 Read article

Stereoselective Catalytic Synthesis of Alkynylated Phosphaethenes Leading to Activation-Free Gold Catalysis

Stereoselective Catalytic Synthesis of Alkynylated Phosphaethenes Leading to Activation‐Free Gold Catalysis

[Full Paper]
Shigekazu Ito, Tomokazu Shinozaki, Koichi Mikami
Eur. J. Org. Chem., December 08, 2017, https://doi.org/10.1002/ejoc.201701259 Read article

Synthesis and Application of Rylene Imide Dyes as Organic Semiconducting Materials

Synthesis and Application of Rylene Imide Dyes as Organic Semiconducting Materials

This Focus Review summarizes the synthesis of a variety of rylene imide derivatives, which have been among the most promising organic semiconducting materials, from different building blocks. Furthermore, their properties and applications are discussed.

[Focus Review]
Jiajing Feng, Wei Jiang, Zhaohui Wang
Chem. Asian J., December 07, 2017, https://doi.org/10.1002/asia.201701424 Read article

Rhodium-Catalyzed Alkenyl C−H Activation and Oxidative Coupling with Allylic Alcohols

Rhodium‐Catalyzed Alkenyl C−H Activation and Oxidative Coupling with Allylic Alcohols

Oxidative coupling of allylic alcohols: [Cp*RhCl2]2 was demonstrated to catalyze the oxidative coupling of alkenylpyridines with allylic alcohols through alkenyl C−H activation in the presence of AgOTf and AgOAc to afford β-alkenyl ketones and aldehydes in moderate to good yields.

[Full Paper]
Rui Yan, Zhong-Xia Wang
Asian J. Org. Chem., December 07, 2017, https://doi.org/10.1002/ajoc.201700515 Read article

The Highly Efficient Suzuki–Miyaura Cross-Coupling of (Hetero)aryl Chlorides and (Hetero)arylboronic Acids Catalyzed by “Bulky-yet-Flexible” Palladium–PEPPSI Complexes in Air

The Highly Efficient Suzuki–Miyaura Cross‐Coupling of (Hetero)aryl Chlorides and (Hetero)arylboronic Acids Catalyzed by “Bulky‐yet‐Flexible” Palladium–PEPPSI Complexes in Air

Bulking up: “Bulky-yet-flexible” Pd–PEPPSI complexes are developed and found to exhibit high reactivity for Suzuki–Miyaura cross-coupling reactions. A wide range of biologically relevant bi(hetero)aryls and poly(hetero)aryls are smoothly installed by using a low loading of the palladium catalyst, a weak base, and aerobic conditions. NHC=N-heterocyclic carbene.

[Communication]
Jia-Sheng Ouyang, Yan-Fang Li, Fei-Dong Huang, Dong-Dong Lu, Feng-Shou Liu
ChemCatChem, December 05, 2017, https://doi.org/10.1002/cctc.201701076 Read article

Efficient Conversion of Bio-Lactic Acid to 2,3-Pentanedione on Cesium-Doped Hydroxyapatite Catalysts with Balanced Acid–Base Sites

Efficient Conversion of Bio‐Lactic Acid to 2,3‐Pentanedione on Cesium‐Doped Hydroxyapatite Catalysts with Balanced Acid–Base Sites

Doping for a better balance: Cesium-doped hydroxyapatite catalysts offers an efficient activity for the condensation of biobased lactic acid to 2,3-pentanedione. The unprecedented catalytic performance relates to the synergy between basic sites and acidic sites located on the surface of the cesium-doped catalyst.

[Full Paper]
Xinli Li, Liangwei Sun, Weixin Zou, Ping Cao, Zhi Chen, Congming Tang, Lin Dong
ChemCatChem, November 29, 2017, https://doi.org/10.1002/cctc.201701332 Read article

Nickel-Catalyzed Directed Benzylation of Ortho C−H Bonds in Aromatic Amides through C−H/C−N Cleavage

Nickel‐Catalyzed Directed Benzylation of Ortho C−H Bonds in Aromatic Amides through C−H/C−N Cleavage

Double action: Cross-coupling of aromatic amides with aryltrimethylammonium salts through the cleavage of both sp2 C−H and C−N bonds is achieved in the presence of 10 mol % of NiBr2 as a simple, inexpensive, and abundant catalyst.

[Communication]
Jiawei Li, Zhaojing Zheng, Tiantian Xiao, Peng-Fei Xu, Hao Wei
Asian J. Org. Chem., November 29, 2017, https://doi.org/10.1002/ajoc.201700569 Read article

Enantioselective Synthesis of the C23–C33 Fragment of Aetheramide A and Its C32 Epimer

Enantioselective Synthesis of the C23–C33 Fragment of Aetheramide A and Its C32 Epimer

The C23–33 fragment of aetheramide A with either the natural (R,R,R) and unnatural (R,S,R) configuration was synthesized from (R)-mandelic acid and 3-iodomethacrylaldehyde through catalytic enantioselective allylation. TBS = tert-butyldimethylsilyl, Bpin = 4,4,5,5-tetramethyl-1,3,2-dioxaborolanyl), (R)-TRIP-PA = (R)-3,3′-Bis(2,4,6-triisopropylphenyl)-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate.

[Communication]
Tibor Peňaška, Petr Koukal, Martin Kotora
Eur. J. Org. Chem., November 28, 2017, https://doi.org/10.1002/ejoc.201701416 Read article

1-Phenyl-1,2-benziodoxol-3-(1H)-one as Synthon for Phthalide Synthesis through Pd-Free, Base-Free, Sonogashira-Type Coupling Cyclization Reaction

1‐Phenyl‐1,2‐benziodoxol‐3‐(1H)‐one as Synthon for Phthalide Synthesis through Pd‐Free, Base‐Free, Sonogashira‐Type Coupling Cyclization Reaction

[Full Paper]
Ahmad A. Almasalma, Esteban Mejía
Eur. J. Org. Chem., November 24, 2017, https://doi.org/10.1002/ejoc.201700940 Read article

Copper-Catalyzed Carbonyl Group Controlled Coupling of Isatin Oximes with Arylboronic Acids To Prepare N-Aryloxindole Nitrones

Copper‐Catalyzed Carbonyl Group Controlled Coupling of Isatin Oximes with Arylboronic Acids To Prepare N‐Aryloxindole Nitrones

An efficient carbonyl group controlled strategy was developed to prepare (E)-N-arylisatin ketonitrones in good to excellent yields from the copper-catalyzed coupling reaction of isatin oximes and arylboronic acids under mild conditions. DCE = 1,2-dichloroethane.

[Full Paper]
Xue-Ling Mo, Chun-Hua Chen, Cui Liang, Dong-Liang Mo
Eur. J. Org. Chem., November 22, 2017, https://doi.org/10.1002/ejoc.201701324 Read article

Benziodoxole Triflate as a Versatile Reagent for Iodo(III)cyclization of Alkynes

Benziodoxole Triflate as a Versatile Reagent for Iodo(III)cyclization of Alkynes

Hyperactive: A benziodoxole triflate promotes iodo(III)cyclization of alkynes tethered to a variety of nucleophilic moieties, affording benziodoxole-appended (hetero)arenes such as benzofurans, benzothiophenes, isocoumarins, indoles, and polyaromatics. These unprecedented (hetero)aryl-IIII compounds are easy to purify, air- and thermally stable, and amenable to various synthetic transformations.

[Communication]
Bin Wu, Junliang Wu, Naohiko Yoshikai
Chem. Asian J., November 20, 2017, https://doi.org/10.1002/asia.201701530 Read article

Pot-Economical Synthesis of Hydroxylated Arylethenyl-arylethynyl-arenes through Sequential Decarboxylative Perkin–Sonogashira Reactions

Pot‐Economical Synthesis of Hydroxylated Arylethenyl‐arylethynyl‐arenes through Sequential Decarboxylative Perkin–Sonogashira Reactions

Harmonious tandem: A skeletally diverse chemical library of hydroxy-substituted arylethenyl-arylethynyl-arenes [C(sp2)−C(sp2) and C(sp2)−C(sp) framework] was prepared in good yields from terminal-alkyne-elaborated halogen-functionalized hydroxylated stilbenes. Their topological connectivity might afford them exceptional optoelectronic and medicinal properties. The products are amenable to downstream modification and can be further utilized for the synthesis of versatile molecular frameworks.

[Full Paper]
Amit Shard, Rajesh Kumar, Danish Equbal, Arun Kumar Sinha
Asian J. Org. Chem., November 17, 2017, https://doi.org/10.1002/ajoc.201700504 Read article

Potentiality and Synthesis of O- and N-Heterocycles: Pd-Catalyzed Cyclocarbonylative Sonogashira Coupling as a Valuable Route to Phthalans, Isochromans, and Isoindolines

Potentiality and Synthesis of O‐ and N‐Heterocycles: Pd‐Catalyzed Cyclocarbonylative Sonogashira Coupling as a Valuable Route to Phthalans, Isochromans, and Isoindolines

[Microreview]
Gianluigi Albano, Laura Antonella Aronica
Eur. J. Org. Chem., October 24, 2017, https://doi.org/10.1002/ejoc.201701041 Read article

Mercaptoaryl-Oxazoline Complexes of Palladium and Their High Activities as Catalysts for Suzuki–Miyaura Coupling Reactions in Water

Mercaptoaryl‐Oxazoline Complexes of Palladium and Their High Activities as Catalysts for Suzuki–Miyaura Coupling Reactions in Water

[Full Paper]
Christof Holzer, Antoine Dupé, Lydia M. Peschel, Ferdinand Belaj, Nadia C. Mösch-Zanetti
Eur. J. Inorg. Chem., October 04, 2017, https://doi.org/10.1002/ejic.201700823 Read article

A Physical-Inorganic Approach for the Elucidation of Active Iron Species and Mechanism in Iron-Catalyzed Cross-Coupling

A Physical‐Inorganic Approach for the Elucidation of Active Iron Species and Mechanism in Iron‐Catalyzed Cross‐Coupling

[Review]
Stephanie H. Carpenter, Michael L. Neidig
Isr. J. Chem., August 24, 2017, https://doi.org/10.1002/ijch.201700036 Read article

Recent Progress in Application of Graphene Supported Metal Nanoparticles in C−C and C−X Coupling Reactions

Recent Progress in Application of Graphene Supported Metal Nanoparticles in C−C and C−X Coupling Reactions

The latest advances in the preparation of graphene supported metal nanoparticles and their application in the catalytic organic transformation of both carbon-carbon (C−C) and carbon-heteroatom (C−X) bonds.

[Personal Account]
Mahmoud Nasrollahzadeh, Zahra Issaabadi, Mohammad Mostafa Tohidi, S. Mohammad Sajadi
Chem. Rec., July 26, 2017, https://doi.org/10.1002/tcr.201700022 Read article

Iron-Catalyzed C−C Bond Formation via Chelation-Assisted C−H Activation

Iron‐Catalyzed C−C Bond Formation via Chelation‐Assisted C−H Activation

[Review]
Naohiko Yoshikai
Isr. J. Chem., July 26, 2017, https://doi.org/10.1002/ijch.201700047 Read article

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