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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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Empirical and Computational Insights into N-Arylation Reactions Catalyzed by Palladium meta-Terarylphosphine Catalyst

Empirical and Computational Insights into N‐Arylation Reactions Catalyzed by Palladium meta‐Terarylphosphine Catalyst

Get cross! The Pd–Cy*Phine catalyst generated in situ was successfully applied to the N-arylation cross-coupling of primary and secondary amines (see figure), and it exhibits high performance across multiple substrate classes. Computational investigations also indicate that a putative rate-determining step occurs after amine binding, which is likely to annul the expected benefits of the meta-terarylphosphine ligand architecture.

[Full Paper]
Fui Fong Yong, Adrian M. Mak, Wenqin Wu, Michael B. Sullivan, Edward G. Robins, Charles W. Johannes, Howard Jong, Yee Hwee Lim
ChemPlusChem, April 28, 2017, https://doi.org/10.1002/cplu.201700042 Read article

Design, Synthesis and Photophysical Property of a Doubly Widened Fused-Triazolyl-Phenanthrene Unnatural Nucleoside

Design, Synthesis and Photophysical Property of a Doubly Widened Fused‐Triazolyl‐Phenanthrene Unnatural Nucleoside

Fused Triazolyl Phenanthrene! is presented as a new generation of doubly widened hydrophobic unnatural nucleobase surrogate having interesting photphysical property with chrysene type emission. Theoretical study based on Molecular dynamics simulation using Schrodinger Macromodel and DFT reveal its potential stacking propensity in a duplex DNA without compromising the right-handed B-form helical conformations with C2′-endo/C3′-exo sugar disposition. Thus, the novel FTPhen is expected to find wide applications in chemistry, biotechnology and DNA-based material design.

[Communication]
Subhendu Sekhar Bag, Suman Kalyan Das
ChemistrySelect, April 27, 2017, https://doi.org/10.1002/slct.201700392 Read article

Synthesis of o-Allyloxy(ethynyl)benzene Derivatives by Cu-Catalyzed Suzuki–Miyaura-Type Reaction and Their Transformations into Heterocyclic Compounds

Synthesis of o‐Allyloxy(ethynyl)benzene Derivatives by Cu‐Catalyzed Suzuki–Miyaura‐Type Reaction and Their Transformations into Heterocyclic Compounds

The Suzuki–Miyaura-type reactions of o-allyloxy(bromoethynyl)benzenes with arylboronic acids using a hydrazone/Cu catalyst system proceeded smoothly in iPrOH under mild conditions to afford the corresponding o-allyloxy(arylethynyl)benzenes. Annulation and enyne metathesis of the o-allyloxy(arylethynyl)benzenes using transition-metal catalysts led to various heterocyclic compounds.

[Full Paper]
Kohei Watanabe, Takashi Mino, Eri Ishikawa, Miyu Okano, Tatsuya Ikematsu, Yasushi Yoshida, Masami Sakamoto, Kazuki Sato, Kazuhiro Yoshida
Eur. J. Org. Chem., April 27, 2017, https://doi.org/10.1002/ejoc.201700217 Read article

Recent Progress in Decarboxylative Oxidative Cross-Coupling for Biaryl Synthesis

Recent Progress in Decarboxylative Oxidative Cross‐Coupling for Biaryl Synthesis

Developing efficient and selective routes for biaryl synthesis is of great interest. Decarboxylative oxidative coupling is appealing, because both substrate classes are readily available, and only CO2 and H2O are formed as side products. Furthermore, the carboxyl group offers a site for selective transformations. This review details decarboxylative oxidative coupling from 2008 to the present.

[Microreview]
Gregory J. P. Perry, Igor Larrosa
Eur. J. Org. Chem., April 26, 2017, https://doi.org/10.1002/ejoc.201700121 Read article

Suzuki–Miyaura Cross-Coupling Reactions of Highly Fluorinated Arylboronic Esters: Catalytic Studies and Stoichiometric Model Reactions on the Transmetallation Step

Suzuki–Miyaura Cross‐Coupling Reactions of Highly Fluorinated Arylboronic Esters: Catalytic Studies and Stoichiometric Model Reactions on the Transmetallation Step

Deserves a metal: The Suzuki–Miyaura cross-coupling reaction of highly fluorinated boronic esters, such as 2-Bpin-C5NF4, was investigated by using [Pd(Me)2(tmeda)] or trans-[PdBr{4-C6H4CH2CH{NHC(O)CH3}CO2Et}(PiPr3)2] as precatalysts. Stoichiometric studies on the transmetallation step revealed the high reactivity of a Pd fluorido derivative towards 2-BpinC5NF4, which leads to the formation of an ionic intermediate and finally yields the cross-coupling product.

[Full Paper]
Johannes Kohlmann, Thomas Braun, Reik Laubenstein, Roy Herrmann
Chem. Eur. J., April 26, 2017, https://doi.org/10.1002/chem.201700549 Read article

A Bioinspired Organocatalytic Cascade for the Selective Oxidation of Amines under Air

A Bioinspired Organocatalytic Cascade for the Selective Oxidation of Amines under Air

Bioinspired Organocatalytic Cascade: Dual mimicking of purpurogallin biosynthesis and copper amine oxidases activity allows the chemoselective oxidative cross-coupling of primary amines to imines under environmentally benign metal-free conditions.

[Communication]
Martine Largeron, Maurice-Bernard Fleury
Chem. Eur. J., April 24, 2017, https://doi.org/10.1002/chem.201701402 Read article

A Method for the Late-Stage Formation of Ketones, Acyloins, and Aldols from Alkenylstannanes: Application to the Total Synthesis of Paecilonic Acid A

A Method for the Late‐Stage Formation of Ketones, Acyloins, and Aldols from Alkenylstannanes: Application to the Total Synthesis of Paecilonic Acid A

Take (it) off: Treatment of alkenylstannanes with Cu(OAc)2/Et3N affords ketones, acyloins, aldols, and enol derivatives under conditions that proved compatible with many common functionalities; these include groups that would neither survive under the standard Tamao–Fleming conditions for the oxidation of Cinline image −SiR3 bonds nor under the conditions commonly used to oxidize C−B bonds. These virtues are illustrated by a concise approach to the bicyclic lipid paecilonic acid A.

[Communication]
Heiko Sommer, James Y. Hamilton, Alois Fürstner
Angew. Chem. Int. Ed., April 24, 2017, https://doi.org/10.1002/anie.201701391 Read article

Palladium-Catalyzed Synthesis and Fluorescence Study of Ethynylated Naphthalene Derivatives

Palladium‐Catalyzed Synthesis and Fluorescence Study of Ethynylated Naphthalene Derivatives

[Full Paper]
Hoang Huy Do, Alexander Villinger, Stefan Lochbrunner, Peter Ehlers, Peter Langer
Eur. J. Org. Chem., April 21, 2017, https://doi.org/10.1002/ejoc.201700024 Read article

Recent Advances in Functionalization of α-C(sp3)–H Centres in Inactivated Ethers through Cross Dehydrogenative Coupling

Recent Advances in Functionalization of α‐C(sp3)–H Centres in Inactivated Ethers through Cross Dehydrogenative Coupling

C–H activation in saturated ethers followed by functionalization with various coupling partners under oxidative conditions has been an area of significant interest. This microreview sheds light on C–C and C–heteroatom bond formation in these inactivated ethers.

[Microreview]
Aanchal Batra, Paramjit Singh, Kamal Nain Singh
Eur. J. Org. Chem., April 20, 2017, https://doi.org/10.1002/ejoc.201700341 Read article

Cobalt(II)/TFA-Catalyzed Oxidative Esterification of Aldehydes and Alcohols: Dual Role of the Acid Co-Catalyst

Cobalt(II)/TFA‐Catalyzed Oxidative Esterification of Aldehydes and Alcohols: Dual Role of the Acid Co‐Catalyst

Dear Ester: A CoII/TFA-catalyzed oxidative esterification of aldehydes and alkanols has been developed that uses tBuOOH as an oxidant. Mechanistic investigation indicated that the formation of a CoIII−OCH(OMe)R complex was the kinetic selectivity-determining step. TFA played a dual role in the cross-coupling reaction, as an external proton source to activate the aldehyde and as a co-catalyst to tune the reactivity of the Co site.

[Full Paper]
Sajid Mahmood, Ting Li, Bao-Hua Xu, Ya-Fei Guo, Suo-Jiang Zhang
Asian J. Org. Chem., April 18, 2017, https://doi.org/10.1002/ajoc.201700139 Read article

Separating Thermodynamics from Kinetics—A New Understanding of the Transketolase Reaction

Separating Thermodynamics from Kinetics—A New Understanding of the Transketolase Reaction

Textbook catalysis revised: The initially kinetically controlled transketolase-catalyzed lithium hydroxypyruvate reaction has been so far mistakenly described as thermodynamic controlled. A new understanding of this effect and of the reasons why hydrophobic substrates are converted by an enzyme that naturally has a high affinity to hydrophilic substrates sheds new light on textbook biocatalysis.

[Full Paper]
Stefan R. Marsden, Lorina Gjonaj, Stephen J. Eustace, Ulf Hanefeld
ChemCatChem, April 13, 2017, https://doi.org/10.1002/cctc.201601649 Read article

Cyclopentanone as an Alternative Linking Reactant for Heterogeneously Catalyzed Furfural Aldol Condensation

Cyclopentanone as an Alternative Linking Reactant for Heterogeneously Catalyzed Furfural Aldol Condensation

The strongest link: The use of cyclopentanone in the synthesis of diesel precursors by furfural aldol condensation is proposed. This reaction is catalyzed by a magnesium–zirconium mixed oxide. To optimize the C15 selectivity, different temperatures and initial furfural/cyclopentanone ratios are tested. Under the optimum conditions, yields for the desired C15 adduct are higher than 60 % in less than 4 h.

[Communication]
Jennifer Cueto, Laura Faba, Eva Díaz, Salvador Ordóñez
ChemCatChem, April 04, 2017, https://doi.org/10.1002/cctc.201601655 Read article

Synthesis of a Silyl Cobalt Hydride and Its Catalytic Performance in Kumada Coupling Reactions

Synthesis of a Silyl Cobalt Hydride and Its Catalytic Performance in Kumada Coupling Reactions

[P,Si]chedelic! Four silyl [P,Si]-chelate cobalt complexes have been synthesized through the chelate-assisted Si−H activation of bidentate preligand ortho-HSi(Me)2(PPh2)C6H4 with CoMe(PMe3)4 and CoCl(PMe3)3. The catalytic performance of complex 5 was explored for Kumada coupling reactions, showing good to excellent catalytic efficiency with 2 mol % catalyst loading for the reactions of aryl chlorides or aryl bromides with Grignard reagents.

[Full Paper]
Shilu Xu, Peng Zhang, Xiaoyan Li, Benjing Xue, Hongjian Sun, Olaf Fuhr, Dieter Fenske
Chem. Asian J., March 30, 2017, https://doi.org/10.1002/asia.201700144 Read article

Cooperation of a Nickel–Bipyridine Complex with Light for Benzylic C−H Arylation of Toluene Derivatives

Cooperation of a Nickel–Bipyridine Complex with Light for Benzylic C−H Arylation of Toluene Derivatives

Gimme the light! Benzylic C−H bonds of toluene derivatives are directly arylated with aryl halides by means of a nickel–dtbbpy catalyst under irradiation with UV light; dtbbpy=4,4′-di-tert-butyl-2,2′-bipyridine.

[Communication]
Naoki Ishida, Yusuke Masuda, Norikazu Ishikawa, Masahiro Murakami
Asian J. Org. Chem., March 21, 2017, https://doi.org/10.1002/ajoc.201700115 Read article

Copper-Catalyzed Synthesis of Tetrasubstituted Allenes from Quaternary Ammonium Salts and Grignard Reagents

Copper‐Catalyzed Synthesis of Tetrasubstituted Allenes from Quaternary Ammonium Salts and Grignard Reagents

Copper proves its worth: Tetrasubstituted allenes have been prepared from the CuBr2-catalyzed reaction of readily available quaternary ammonium salts and Grignard reagents. The reaction proceeds smoothly giving products in good to excellent yields (see scheme).

[Communication]
Shengming Ma, Qi Liu, Xinjun Tang, Yujuan Cai
Asian J. Org. Chem., February 17, 2017, https://doi.org/10.1002/ajoc.201600620 Read article

Palladium-Catalyzed Chemoselective Switch: Synthesis of a New Class of Indenochromenes and Pyrano[2,3-c]carbazoles

Palladium‐Catalyzed Chemoselective Switch: Synthesis of a New Class of Indenochromenes and Pyrano[2,3‐c]carbazoles

1-2-Switch: A complementary set of Pd-based catalyst systems has been developed for the synthesis of two different pyran-annulated polyheterocycles, indeno[1,2,3-de]chromenes, and pyrano[2,3-c]carbazoles from a common intermediate.

[Full Paper]
K. Ranjith Reddy, Prakash Kannaboina, Parthasarathi Das
Asian J. Org. Chem., February 14, 2017, https://doi.org/10.1002/ajoc.201600530 Read article

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