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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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Visible-Light Photocatalysis as an Enabling Tool for the Functionalization of Unactivated C(sp3)-Substrates

Visible‐Light Photocatalysis as an Enabling Tool for the Functionalization of Unactivated C(sp3)‐Substrates

[Microreview]
Sara Roslin, Luke R. Odell
Eur. J. Org. Chem., February 20, 2017, DOI: 10.1002/ejoc.201601479. Read article

Twisted Amides: From Obscurity to Broadly Useful Transition-Metal-Catalyzed Reactions by N−C Amide Bond Activation

Twisted Amides: From Obscurity to Broadly Useful Transition‐Metal‐Catalyzed Reactions by N−C Amide Bond Activation

Twist of faith! Recently the use of amide bond twist (distortion) has advanced to the general organic chemistry mainstream enabling a host of highly attractive N−C amide bond cross-coupling reactions of broad synthetic relevance. In this Minireview, recent progress in this area is discussed and a detailed overview of the prominent role of amide bond destabilization as a driving force in the development of transition-metal-catalyzed cross-coupling reactions by N−C amide bond activation is presented.

[Minireview]
Chengwei Liu, Michal Szostak
Chem. Eur. J., February 20, 2017, DOI: 10.1002/chem.201605012. Read article

Visible-Light-Promoted Asymmetric Cross-Dehydrogenative Coupling of Tertiary Amines to Ketones by Synergistic Multiple Catalysis

Visible‐Light‐Promoted Asymmetric Cross‐Dehydrogenative Coupling of Tertiary Amines to Ketones by Synergistic Multiple Catalysis

Working together: Synergistic multiple catalytic cycles enable an asymmetric cross-dehydrogenative coupling between tertiary amines and simple ketones with high diastereo- and enantioselectivity under visible-light irradiation. This process is enabled by a simple chiral primary amine catalyst through the coupling of a catalytic enamine intermediate and an iminium cation intermediate in situ generated from tetrahydroisoquinoline derivatives by Ru/Co catalysis.

[Communication]
Qi Yang, Long Zhang, Chen Ye, Sanzhong Luo, Li-Zhu Wu, Chen-Ho Tung
Angew. Chem. Int. Ed., February 17, 2017, DOI: 10.1002/anie.201700572. 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, DOI: 10.1002/ajoc.201600620. Read article

Palladium-Mediated Arylation of Lysine in Unprotected Peptides

Palladium‐Mediated Arylation of Lysine in Unprotected Peptides

Defenses down: In the presence of a preformed biarylphosphine-supported palladium(II)–aryl complex and a weak base, lysine amino groups in unprotected peptides underwent C−N bond formation at room temperature (see scheme). The process was applicable to the conjugation of a variety of organic compounds, including complex drug molecules, to peptides and was also successfully applied to the formation of cyclic peptides through macrocyclization.

[Communication]
Hong Geun Lee, Guillaume Lautrette, Bradley L. Pentelute, Stephen L. Buchwald
Angew. Chem. Int. Ed., February 16, 2017, DOI: 10.1002/anie.201611202. Read article

Synthesis of 2,2,2,-Trichloroethyl Aryl- and Vinyldiazoacetates by Palladium-Catalyzed Cross-Coupling

Synthesis of 2,2,2,‐Trichloroethyl Aryl‐ and Vinyldiazoacetates by Palladium‐Catalyzed Cross‐Coupling

Making TCE: 2,2,2-Trichloroethyl (TCE) aryl- and vinyldiazoacetates have recently emerged as versatile reagents for rhodium-carbene chemistry. Herein, an efficient and convenient synthesis of TCE aryl- and vinyldiazoacetates by palladium-catalyzed cross-coupling reactions between TCE diazoacetates and aryl or vinyl iodides is reported.

[Communication]
Liangbing Fu, Jeffrey D. Mighion, Eric A. Voight, Huw M. L. Davies
Chem. Eur. J., February 15, 2017, DOI: 10.1002/chem.201700101. Read article

Palladium-Mediated Labeling of Nucleic Acids

Palladium‐Mediated Labeling of Nucleic Acids

DNA probes: New applications of Pd-catalyzed coupling reactions for post-conjugation of nucleic acids have been developed recently. Breakthroughs in this area might now pave the way for the development of sophisticated DNA probes potentially of great interest in chemical biology, nanotechnology, and bioanalysis, as well as in diagnostic domains.

[Minireview]
Eric Defrancq, Samir Messaoudi
ChemBioChem, February 14, 2017, DOI: 10.1002/cbic.201600599. Read article

Oxygen Activated, Palladium Nanoparticle Catalyzed, Ultrafast Cross-Coupling of Organolithium Reagents

Oxygen Activated, Palladium Nanoparticle Catalyzed, Ultrafast Cross‐Coupling of Organolithium Reagents

No oxygen, no coupling: Molecular oxygen was shown to be crucial for the fast palladium-catalyzed cross-coupling of organolithium reagents developed herein. Reactions times down to 5 s provide a novel procedure for the preparation of radiolabeled compounds.

[Communication]
Dorus Heijnen, Filippo Tosi, Carlos Vila, Marc C. A. Stuart, Philip H. Elsinga, Wiktor Szymanski, Ben L. Feringa
Angew. Chem. Int. Ed., February 14, 2017, DOI: 10.1002/anie.201700417. 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, DOI: 10.1002/ajoc.201600530. Read article

Development of Highly Potent GAT1 Inhibitors: Synthesis of Nipecotic Acid Derivatives with N-Arylalkynyl Substituents

Development of Highly Potent GAT1 Inhibitors: Synthesis of Nipecotic Acid Derivatives with N‐Arylalkynyl Substituents

Stable alkyne-type spacer: A series of N-substituted nipecotic acid derivatives with various 2-biphenyl moieties attached via an N-alkynyl linker were synthesized as potential GAT1 inhibitors. Some 2′,4′-disubstituted derivatives were found to be highly potent in binding and uptake assays and display high subtype selectivity for GAT1.

[Full Paper]
Toni Lutz, Thomas Wein, Georg Höfner, Klaus T. Wanner
ChemMedChem, February 10, 2017, DOI: 10.1002/cmdc.201600599. Read article

A Hydrazone-Based Covalent Organic Framework as an Efficient and Reusable Photocatalyst for the Cross-Dehydrogenative Coupling Reaction of N-Aryltetrahydroisoquinolines

A Hydrazone‐Based Covalent Organic Framework as an Efficient and Reusable Photocatalyst for the Cross‐Dehydrogenative Coupling Reaction of N‐Aryltetrahydroisoquinolines

Heterogeneous COF photocatalyst: A hydrazone-based covalent organic framework (COF) is employed as a highly efficient, recyclable heterogeneous photocatalyst in cross-dehydrogenative coupling (CDC) reactions. This approach highlights the potential of developing photoactive COFs as highly active photocatalysts for a variety of important organic transformations.

[Communication]
Wanting Liu, Qing Su, Pengyao Ju, Bixuan Guo, Hui Zhou, Guanghua Li, Qiaolin Wu
ChemSusChem, February 07, 2017, DOI: 10.1002/cssc.201601702. Read article

Construction of Tertiary Amides: NiII-Catalyzed N-Arylation of Secondary Acyclic Amides (2-Picolinamides) with Aryl Halides

Construction of Tertiary Amides: NiII‐Catalyzed N‐Arylation of Secondary Acyclic Amides (2‐Picolinamides) with Aryl Halides

Chelation-assisted C−N cross coupling: N-arylation of secondary acyclic amides with aryl halides using relatively inexpensive NiCl2 as a catalyst has been reported for the synthesis of various tertiary amides.

[Communication]
Rathinam Sankar, Srinivasarao Arulananda Babu
Asian J. Org. Chem., February 03, 2017, DOI: 10.1002/ajoc.201600596. Read article

Mechanistic Studies of Ullmann-Type C–N Coupling Reactions: Carbonate-Ligated Copper(III) Intermediates

Mechanistic Studies of Ullmann‐Type C–N Coupling Reactions: Carbonate‐Ligated Copper(III) Intermediates

Triple role of carbonate: A mechanism is proposed for the Ullmann C−N coupling based on the direct observation of CuIII intermediates in the UV/Vis and FTIR spectra. CO32− is a second ligand and facilitates the reductive elimination. Actual intermediate species are distorted octahedral CuIII complexes. Experimental results are complimented by DFT calculations.

[Full Paper]
Kamlesh K. Gurjar, Rajendra K. Sharma
ChemCatChem, January 31, 2017, DOI: 10.1002/cctc.201601174. Read article

Insights into the Scholl Coupling Reaction: A Key Transformation of Relevance to the Synthesis of Graphenes and Related Systems

Insights into the Scholl Coupling Reaction: A Key Transformation of Relevance to the Synthesis of Graphenes and Related Systems

Scholl coupling reactions proceed by unexpected oxidation/coupling pathways.

[Full Paper]
Mark S. Little, Stephen G. Yeates, Aula A. Alwattar, Kane W. J. Heard, James Raftery, Alyn C. Edwards, Adam. V. S. Parry, Peter Quayle
Eur. J. Org. Chem., January 30, 2017, DOI: 10.1002/ejoc.201601580. Read article

Visible-Light Photoredox Decarboxylative Couplings

Visible‐Light Photoredox Decarboxylative Couplings

Good morning sunshine! Visible-light photoredox decarboxylative coupling reactions have become an important chemical transformation because of their wide substrate scope, mild reaction conditions, high efficiency, and practicability. Herein, we have summarized recent advances in this synthetic strategy, which include details regarding the formation of C−C and C−Y (Y=heteroatom) bonds.

[Focus Review]
Yunhe Jin, Hua Fu
Asian J. Org. Chem., January 23, 2017, DOI: 10.1002/ajoc.201600513. Read article

Emergence of Unactivated Olefins for the Synthesis of Olefinated Arenes

Emergence of Unactivated Olefins for the Synthesis of Olefinated Arenes

Overdependence on electronically biased activated olefins is a key drawback of Mizoroki–Heck and Fujiwara–Moritani coupling. With unbiased aliphatic olefins, inability to control regio- and stereoselectivity greatly restricts their application. Recent significant advances in olefination with unactivated alkenes to synthesize both linear and branched olefin products are outlined in this review.

[Microreview]
Arghya Deb, Debabrata Maiti
Eur. J. Org. Chem., December 30, 2016, DOI: 10.1002/ejoc.201601253. Read article

Pd-PEPPSI-IPentCl-Catalyzed Amination Using Aminotriphenylsilane as an Ammonia Surrogate

Pd‐PEPPSI‐IPentCl‐Catalyzed Amination Using Aminotriphenylsilane as an Ammonia Surrogate

Triphenylsilyl-protected anilines were obtained from the cross-coupling of aminotriphenylsilane with aryl halides in the presence of Pd-PEPPSI-IPentCl {dichloro(3-chloropyridyl)[4,5-dichloro-1,3-bis(2,6-dipent-3-ylphenyl)imidazol-2-ylidene]palladium(II)}. The silylated products were then alkylated without over-alkylation, yielding the secondary amines after hydrolysis under mild acidic conditions.

[Communication]
Christopher Lombardi, David Mitchell, Michael J. Rodriguez, Michael G. Organ
Eur. J. Org. Chem., December 28, 2016, DOI: 10.1002/ejoc.201601565. Read article

Sunflow: Sunlight Drives Fast and Green Photochemical Flow Reactions in Simple Microcapillary Reactors – Application to Photoredox and H-Atom-Transfer Chemistry

Sunflow: Sunlight Drives Fast and Green Photochemical Flow Reactions in Simple Microcapillary Reactors – Application to Photoredox and H‐Atom‐Transfer Chemistry

“Sunflow” – The combination of a microcapillary reactor and sunlight enables fast and green photoredox and H-atom-transfer reactions in continuous flow. Kinetic studies reveal high reaction rates with a simple and inexpensive reactor setup (less than 90 USD acquisition value).

[Communication]
Alexander M. Nauth, Alexander Lipp, Benjamin Lipp, Till Opatz
Eur. J. Org. Chem., December 28, 2016, DOI: 10.1002/ejoc.201601394. Read article

Synthesis of Covalently Linked Oligo(phenyleneethynylene) Wires Incorporating Dithiafulvene Units: Redox-Active “H-Cruciforms”

Synthesis of Covalently Linked Oligo(phenyleneethynylene) Wires Incorporating Dithiafulvene Units: Redox‐Active “H‐Cruciforms”

The synthesis of large π-conjugated motifs based on two parallel oligo(phenyleneethynylene)s (OPEs) and an orthogonally situated redox-active stilbene-extended tetrathiafulvalene (TTF) is presented. The OPEs are end-capped with thioester groups as potential electrode anchoring groups.

[Full Paper]
Frederik Præstholm Jørgensen, Johannes F. Petersen, Cecilie Lindholm Andersen, Anders B. Skov, Martyn Jevric, Ole Hammerich, Mogens Brøndsted Nielsen
Eur. J. Org. Chem., December 13, 2016, DOI: 10.1002/ejoc.201601367. Read article

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