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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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Palladium-Catalyzed Cascade Saegusa–Heck Reaction: Synthesis of β,β-Diarylacroleins from Arylpropanals and Aryl Iodides

Palladium‐Catalyzed Cascade Saegusa–Heck Reaction: Synthesis of β,β‐Diarylacroleins from Arylpropanals and Aryl Iodides

An efficient Pd-catalyzed Saegusa–Heck cascade protocol for the preparation of synthetically useful β,β-diarylacroleins in moderate to high yields (30–83 %) from arylpropanals and aryl iodides is developed.

[Communication]
Li Xiao, Yilin Zheng, Qiong Xie, Liming Shao
Eur. J. Org. Chem., October 18, 2017, https://doi.org/10.1002/ejoc.201701025 Read article

Hybrid Surfactants with N-Heterocyclic Carbene Heads as a Multifunctional Platform for Interfacial Catalysis

Hybrid Surfactants with N‐Heterocyclic Carbene Heads as a Multifunctional Platform for Interfacial Catalysis

Soapy catalyst in action: An organic–inorganic hybrid surfactant containing a carbene-Pd complex as a head is used for micellar catalysis bridging the gap for substrates with orthogonal solvent-compatibility (see figure).

[Communication]
Adrian Donner, Kay Hagedorn, Lorenz Mattes, Markus Drechsler, Sebastian Polarz
Chem. Eur. J., October 18, 2017, https://doi.org/10.1002/chem.201703902 Read article

NIR-Absorbing Donor–Acceptor Based 1,1,4,4-Tetracyanobuta-1,3-Diene (TCBD)- and Cyclohexa-2,5-Diene-1,4-Ylidene-Expanded TCBD-Substituted Ferrocenyl Phenothiazines

NIR‐Absorbing Donor–Acceptor Based 1,1,4,4‐Tetracyanobuta‐1,3‐Diene (TCBD)‐ and Cyclohexa‐2,5‐Diene‐1,4‐Ylidene‐Expanded TCBD‐Substituted Ferrocenyl Phenothiazines

Easy to tune: A series of unsymmetrical and symmetrical donor–acceptor phenothiazines were designed and synthesized by a [2+2] cycloaddition–electrocyclic ring-opening reaction of ferrocenyl-substituted phenothiazines with tetracyanoethylene and 7,7,8,8-tetracyanoquinodimethane. A strong charge-transfer interaction in the phenothiazine derivatives can be tuned by varying the number of TCNE/TCNQ acceptors.

[Full Paper]
Madhurima Poddar, Rajneesh Misra
Chem. Asian J., October 18, 2017, https://doi.org/10.1002/asia.201700879 Read article

Fast, Efficient and Low E-Factor One-Pot Palladium-Catalyzed Cross-Coupling of (Hetero)Arenes

Fast, Efficient and Low E‐Factor One‐Pot Palladium‐Catalyzed Cross‐Coupling of (Hetero)Arenes

Quick-and-clean: The cross-coupling of distinct (hetero)arenes is achieved in a rapid and efficient manner under ambient conditions with very little waste. By using a Pd catalyst and t-BuLi, many polyaromatic compounds are obtained including highly sterically hindered ones. Of these, several are advanced intermediates for widely used chiral Brønsted acid catalysts normally obtained via a rather cumbersome process.

[Communication]
Erik B. Pinxterhuis, Paco Visser, Iwan Esser, Jean-Baptiste Gualtierotti, Ben L. Feringa
Angew. Chem. Int. Ed., October 18, 2017, https://doi.org/10.1002/anie.201707760 Read article

Transition-Metal-Free Reaction of Aryltrimethylammonium Iodides with Arylzinc Reagents

Transition‐Metal‐Free Reaction of Aryltrimethylammonium Iodides with Arylzinc Reagents

Zincing or Iodeling? Reaction of aryltrimethylammonium iodides with arylzinc reagents in the absence of a transition-metal catalyst was performed. The reaction is applicable to a broad scope of substrates and shows good compatibility of functional groups.

[Communication]
Wei-Can Dai, Zhong-Xia Wang
Chem. Asian J., October 17, 2017, https://doi.org/10.1002/asia.201701342 Read article

Palladium-Catalyzed 2,2,2-Trifluoroethoxylation of Aromatic and Heteroaromatic Chlorides Utilizing Borate Salt and the Synthesis of a Trifluoro Analogue of Sildenafil

Palladium‐Catalyzed 2,2,2‐Trifluoroethoxylation of Aromatic and Heteroaromatic Chlorides Utilizing Borate Salt and the Synthesis of a Trifluoro Analogue of Sildenafil

Fluorine Blue: A novel palladium-catalyzed trifluorethyoxylation of aryl chlorides was developed with the aid of a new type of borate-based trifluoroethoxylating reagent. Beyond the functionalization of various aromatic and heteroaromatic systems, the synthesis of the trifluoro analogue of Sidenafil (Viagra) was achieved together with the determination of its physicochemical properties.

[Communication]
Bálint Pethő, Márton Zwillinger, János T. Csenki, Anna E. Káncz, Balázs Krámos, Judit Müller, György T. Balogh, Zoltán Novák
Chem. Eur. J., October 13, 2017, https://doi.org/10.1002/chem.201704205 Read article

Cobalt-Catalyzed Cross-Dehydrogenative C(sp2)−C(sp3) Coupling of Oxazole/Thiazole with Ether or Cycloalkane

Cobalt‐Catalyzed Cross‐Dehydrogenative C(sp2)−C(sp3) Coupling of Oxazole/Thiazole with Ether or Cycloalkane

Direct C5-alkylation of oxazole/thiazole with ether or cycloalkane through a cobalt-catalyzed cross-dehydrogenative coupling (CDC) process is reported. This transformation represents the first C(sp2)−C(sp3) cross-coupling at the C5-position of the azole via double C−H bond cleavages. A preliminary mechanism involving a radical process has also been proposed.

[Communication]
Xiaojiao Wang, Bowen Lei, Lifang Ma, Lisi Zhu, Xinyue Zhang, Hao Zuo, Dailin Zhuang, Ziyuan Li
Chem. Asian J., October 13, 2017, https://doi.org/10.1002/asia.201701258 Read article

Rapid “Mix-and-Stir” Preparation of Well-Defined Palladium on Carbon Catalysts for Efficient Practical Use

Rapid “Mix‐and‐Stir” Preparation of Well‐Defined Palladium on Carbon Catalysts for Efficient Practical Use

DIY catalysts: Efficient Pd/Carbon catalysts are prepared using a simple experimental procedure based on the direct deposition of Pd0 species from a commercially available tris(dibenzylideneacetone)dipalladium(0) complex. Application in cross-coupling and hydrogenation reactions and easy catalyst recycling are demonstrated.

[Full Paper]
Sergey A. Yakukhnov, Evgeniy O. Pentsak, Konstantin I. Galkin, Roman M. Mironenko, Vladimir A. Drozdov, Vladimir A. Likholobov, Valentine P. Ananikov
ChemCatChem, October 10, 2017, https://doi.org/10.1002/cctc.201700738 Read article

Sodium Iodide (NaI)-Catalyzed Cross-Coupling for C−S Bond Formation via Oxidative Dehydrogenation: Cheap, Direct Access to Unsymmetrical Aryl Sulfides

Sodium Iodide (NaI)‐Catalyzed Cross‐Coupling for C−S Bond Formation via Oxidative Dehydrogenation: Cheap, Direct Access to Unsymmetrical Aryl Sulfides

A breath of fresh air: An operationally simple and environmentally friendly sodium-iodide-catalyzed direct C−H sulfenylation of arenes with highly regioselective has been developed under open air.

[Communication]
Hui-Hong Wang, Tao Shi, Wei-Wei Gao, Yong-Qiang Wang, Jun-Fang Li, Yi Jiang, Yong Sheng Hou, Chen Chen, Xue Peng, Zhen Wang
Chem. Asian J., October 10, 2017, https://doi.org/10.1002/asia.201701163 Read article

Nickel-Catalyzed C−N Cross-Coupling of Primary Imines with Subsequent In Situ [2+2] Cycloaddition or Alkylation

Nickel‐Catalyzed C−N Cross‐Coupling of Primary Imines with Subsequent In Situ [2+2] Cycloaddition or Alkylation

Knights who say Ni: A new method for the C−N cross-coupling of aryl chlorides with primary imines by using an air-stable nickel(0) catalyst is reported. This process can be readily coupled with a Staudinger reaction or an alkylation step.

[Full Paper]
Dennis J. Power, Kieran D. Jones, Sven S. Kampmann, Gavin R. Flematti, Scott G. Stewart
Asian J. Org. Chem., October 09, 2017, https://doi.org/10.1002/ajoc.201700464 Read article

Iron-Catalyzed C−O Bond Activation: Opportunity for Sustainable Catalysis

Iron‐Catalyzed C−O Bond Activation: Opportunity for Sustainable Catalysis

Increasing tolerance: Tremendous progress has been achieved in the development of new methods for sustainable functional-group-tolerant iron-catalyzed cross-coupling reactions by selective C−O cleavage. These methods establish highly attractive alternatives to traditional cross-couplings. The most recent advances in sustainable iron-catalyzed cross-couplings of C−O based electrophiles are reviewed, with a focus on mechanistic aspects and synthetic utility.

[Minireview]
Elwira Bisz, Michal Szostak
ChemSusChem, October 05, 2017, https://doi.org/10.1002/cssc.201701287 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

Front Cover: Robust Palladium-Catalyzed Arylation of Catalyst-Poisoning ortho-Sulfanyl Aryl Halides with Tetraarylborates and Its Application to Synthesis of π-Extended Dibenzothiophenes (Asian J. Org. Chem. 10/2017)

Front Cover: Robust Palladium‐Catalyzed Arylation of Catalyst‐Poisoning ortho‐Sulfanyl Aryl Halides with Tetraarylborates and Its Application to Synthesis of π‐Extended Dibenzothiophenes (Asian J. Org. Chem. 10/2017)

Arylation: Palladium-catalyzed arylation of ortho-sulfanyl aryl halides with sodium tetraarylborates proceeds smoothly without any additional bases in high yields, providing a reliable route to 2-sulfanylbiaryls. This protocol offers a practical solution to overcome the poisoning behavior of aryl sulfides with palladium species. The conditions worked well with various halides and functional groups. This strategy provides a short and efficient route to dibenzothiophenes through Pummerer-type cyclization. More information can be found in the Communication by Hideki Yorimitsu et al. on page 1390 in Issue 10, 2017 (DOI: 10.1002/ajoc.201700323).

[Cover Picture]
Dhananjayan Vasu, Jan Niklas Hausmann, Hayate Saito, Tomoyuki Yanagi, Hideki Yorimitsu, Atsuhiro Osuka
Asian J. Org. Chem., September 28, 2017, https://doi.org/10.1002/ajoc.201700514 Read article

Acyl Donors and Additives for the Biocatalytic Friedel–Crafts Acylation

Acyl Donors and Additives for the Biocatalytic Friedel–Crafts Acylation

A biocatalytic Friedel–Crafts-like acylation is described. The scope of the activating groups of the acetyl donors as well as the influence and effect of amines as additive on the reaction are studied.

[Full Paper]
Nina G. Schmidt, Wolfgang Kroutil
Eur. J. Org. Chem., September 19, 2017, https://doi.org/10.1002/ejoc.201701079 Read article

Flow-Assisted Synthesis: A Key Fragment of SR 142948A

Flow‐Assisted Synthesis: A Key Fragment of SR 142948A

Multi-step flow-assisted synthesis of an advanced hydrazine building block utilized in the preparation of SR 142948A.

[Full Paper]
Matthew O. Kitching, Olivia E. Dixon, Marcus Baumann, Ian R. Baxendale
Eur. J. Org. Chem., September 08, 2017, https://doi.org/10.1002/ejoc.201700904 Read article

Nickel-Catalyzed C−H Heteroarylation of Chiral Oxazolines

Nickel‐Catalyzed C−H Heteroarylation of Chiral Oxazolines

It only costs a nickel! A nickel-catalyzed C−H heteroarylation at the 2 position of oxazolines with heteroaryl halides is described. This method is an efficient synthesis for various oxazoline-containing multidentate chiral ligands.

[Communication]
Peng Lu, Chong-Lei Ji, Zhan Lu
Asian J. Org. Chem., September 06, 2017, https://doi.org/10.1002/ajoc.201700446 Read article

Solvent-Controlled Copper-Catalyzed Radical Decarboxylative Coupling for Alkenyl C(sp2)−P Bond Formation

Solvent‐Controlled Copper‐Catalyzed Radical Decarboxylative Coupling for Alkenyl C(sp2)−P Bond Formation

A choosy couple: The solvent-controlled copper-catalyzed oxidative decarboxylative coupling of alkenyl acids with P(O)H compounds has been developed for alkenyl C(sp2)−P bond formation through a free-radical process. On the basis of the catalytic system, styrenes and P(O)H compounds can also be selectively transformed into the desired (E)-alkenylphosphonates and β-ketophosphonates by cross-dehydrogenative coupling and oxyphosphorylation, respectively.

[Full Paper]
Lin Tang, Lixian Wen, Tian Sun, Di Zhang, Zhen Yang, Chengtao Feng, Zhiyong Wang
Asian J. Org. Chem., August 30, 2017, https://doi.org/10.1002/ajoc.201700434 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

C(sp2)−O Bond Formation through a Nickel-Catalyzed Cross-Coupling Reaction in Water Enabled by Micellar Catalysis

C(sp2)−O Bond Formation through a Nickel‐Catalyzed Cross‐Coupling Reaction in Water Enabled by Micellar Catalysis

Ni hao: A Ni-catalyzed reaction between aryl chlorides and alcohols that resulted in C−O bond formation is described. Aromatic and aliphatic alcohols were tolerated effectively, thereby affording a range of ethers in high yields and selectivities.

[Full Paper]
Dini Ahanthem, Warjeet S. Laitonjam
Asian J. Org. Chem., August 24, 2017, https://doi.org/10.1002/ajoc.201700324 Read article

Metal-Catalyzed Synthesis of 1,1-Diarylethylene Scaffolds

Metal‐Catalyzed Synthesis of 1,1‐Diarylethylene Scaffolds

The young 1,1s: This Focus Review summarizes the state-of-the-art metal-catalyzed processes that permit the formation of 1,1-diarylethylene frameworks.

[Focus Review]
Timothée Naret, Olivier Provot, Mouad Alami, Abdallah Hamze
Asian J. Org. Chem., August 21, 2017, https://doi.org/10.1002/ajoc.201700342 Read article

Microwave-Promoted Metal-Free α-Alkylation of Ketones with Cycloalkanes through Cross-Coupling of C(sp3)−H Bonds

Microwave‐Promoted Metal‐Free α‐Alkylation of Ketones with Cycloalkanes through Cross‐Coupling of C(sp3)−H Bonds

Rising to the challenge: The microwave-promoted α-alkylation of ketones with cycloalkanes as alkylating agents under metal-free conditions is presented. This selective cross-coupling of different carbon radicals is a challenge because of the inherent instability and reactivity of these intermediates. The cross-coupling of C(sp3)−H bonds described herein provides a successful example of the realization of this difficult task.

[Full Paper]
Qian-Qian Wang, Zhang-Xin Wang, Xin-Ying Zhang, Xue-Sen Fan
Asian J. Org. Chem., August 09, 2017, https://doi.org/10.1002/ajoc.201700256 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

Robust Palladium-Catalyzed Arylation of Catalyst-Poisoning ortho-Sulfanyl Aryl Halides with Tetraarylborates and Its Application to Synthesis of π-Extended Dibenzothiophenes

Robust Palladium‐Catalyzed Arylation of Catalyst‐Poisoning ortho‐Sulfanyl Aryl Halides with Tetraarylborates and Its Application to Synthesis of π‐Extended Dibenzothiophenes

Poison-resistant reaction: Bis(tri-tert-butylphosphine)palladium-catalyzed arylation of ortho-sulfanyl aryl halides with sodium tetraarylborates proceeds smoothly without any additional bases in high yields, providing a reliable route to 2-sulfanylbiaryls. This arylation protocol offers a practical solution to overcome the poisoning behavior of aryl sulfides in such cross-coupling arylation.

[Communication]
Dhananjayan Vasu, Jan Niklas Hausmann, Hayate Saito, Tomoyuki Yanagi, Hideki Yorimitsu, Atsuhiro Osuka
Asian J. Org. Chem., July 17, 2017, https://doi.org/10.1002/ajoc.201700323 Read article

Convenient Access to C4-Dicarbonylation of Anilines by Iodine-Promoted Oxidative Cross-Coupling Reactions

Convenient Access to C4‐Dicarbonylation of Anilines by Iodine‐Promoted Oxidative Cross‐Coupling Reactions

An innovative route for the construction of C4-dicarbonylation of anilines from simple and readily available anilines and phenyl acetylene has been developed. The iodine-promoted oxidative cross-coupling reaction performed well and the highlight of this protocol was not N−H functionalization but C−H functionalization of unprotected anilines.

[Full Paper]
Panpan Wang, Yajie Fu, Ping Wu, Xin Guo, Baohua Chen
Asian J. Org. Chem., July 05, 2017, https://doi.org/10.1002/ajoc.201700212 Read article

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