Recent advances in the synthesis of aromatic nitro compounds
Guobing Yan and Minghua Yang
DOI: 10.1039/c3ob27354g  

Free to access for 4 weeks

Facile dimethylarsenic exchange and pyramidal inversion in its cysteine and glutathione adducts
D. Scott Bohle and Yuxuan Gu
DOI: 10.1039/c3ob40268a 

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PEGylation enables the specific tumor accumulation of a peptide identified by phage display
Walter Mier, Susanne Krämer, Sabine Zitzmann, Annette Altmann, Karin Leotta, Ursula Schierbaum, Martina Schnölzer, Michael Eisenhut and Uwe Haberkorn
DOI: 10.1039/c3ob27475f  

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Synthetic use of the primary kinetic isotope effect in hydrogen atom transfer 2: generation of captodatively stabilised radicals
Mark E. Wood, Sabine Bissiriou, Christopher Lowe and Kim M. Windeatt
DOI: 10.1039/c3ob40275d  

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We are delighted to have received the authors’ comments from Christopher S. P. McErlean on the recently published HOT article “Revitalizing the aromatic aza-Claisen rearrangement: implications for the mechanism of ‘on-water’ catalysis”.

“Chemistry creates. It is the only discipline in which you can design or imagine a new entity and then go away and build it. Of course, it is always easier said than done, so synthetic organic chemists spend a good deal of their time exploring ways to build molecules more efficiently. That’s what the McErlean Research Group does at the University of Sydney. We are primarily focused on making synthesis easier.

Every undergraduate chemist knows that the aromatic Claisen rearrangement is a great way to build functionalized phenols. The reaction is so prevalent in heterocycle synthesis that we tend not to reference the original work – it is assumed knowledge. Our group envisaged that the aromatic aza-Claisen rearrangement would be an equally powerful way to make functionalised anilines, but the known reaction conditions are just too forcing to be useful.

“On-water” reactions rely on interfacial water to catalyze chemical transformations. Exactly how the interfacial water does this has been the source of much recent debate. Most of the protagonists have relied on computationally derived evidence to support one theory or another. We thought that we could kill two birds with one stone by using on-water catalysis to facilitate the aromatic aza-Claisen rearrangement and probe the kinetics of this transformation.

The outcomes of our work are twofold: an easy way to build functionalised naphthylamines and anilines, and experimental evidence that supports the acid-catalyzed nature of on water chemistry.

We hope that chemists employ this operationally simple synthetic tool to build life-changing molecules, and we hope that our results will spur more experimental chemists to provide hard data regarding the on-water phenomenon.”

This Communication is free to access for the next 4 weeks!

Revitalizing the aromatic aza-Claisen rearrangement: implications for the mechanism of ‘on-water’ catalysis
Kaitlin D. Beare and Christopher S. P. McErlean
DOI: 10.1039/C3OB40118A   

Interested in Christopher S. P. McErlean‘s research? Why not also read these recently published articles:

An in-water, on-water domino process for synthesis
Norcott, Philip; Spielman, Calan; McErlean, Christopher S. P.
Green Chem., 2012, 14, 605.
DOI: 10.1039/c2gc16259h

Total synthesis of C-19 lipid diols containing a 2,5-disubstituted-3-oxygenated tetrahydrofuran
Nesbitt, Caroline L.; McErlean, Christopher S. P.
Org. Biomol. Chem., 2011, 9, 2198.
DOI: 10.1039/c0ob00754d

Revitalizing the aromatic aza-Claisen rearrangement: implications for the mechanism of ‘on-water’ catalysis
Kaitlin D. Beare and Christopher S. P. McErlean
DOI: 10.1039/C3OB40118A   

Free to access for 4 weeks  

Reversible protein affinity-labelling using bromomaleimide-based reagents
Ramiz I. Nathani, Vijay Chudasama, Chris P. Ryan, Paul R. Moody, Rachel E. Morgan, Richard J. Fitzmaurice, Mark E. B. Smith, James R. Baker and Stephen Caddick
DOI: 10.1039/C3OB40239H 

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In this HOT article, Rao and co-workers report a novel Rh(II) and Ru(II) catalysed regio- and chemoselective C-H oxygenation for the facile synthesis of a variety of functionalised phenols from easily accessible arenes. The reaction demonstrates excellent reactivity, ortho-selectivity, good functional group tolerance and high yields. This practical method allowed the synthesis of a few 2-acylphenols in gram-scale and its utility has been well exemplified in further applications in heterocycle synthesis and direct modification of drug Fenofibrate.

Broadening the catalyst and reaction scope of region- and chemoselective C–H oxygenation: a convenient and scalable approach to 2-acylphenols by intriguing Rh(II) and Ru(II) catalysis
Gang Shan, Xuesong Han, Yun Lin, Shanyou Yu and Yu Rao
DOI: 10.1039/C3OB27457H

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In this HOT paper, Blagg and coworkers at the Institute of Cancer Research, Sutton, report an efficient C2-functionalisation via direct C–H arylation for N3-MEM-protected imidazo[4,5-b]pyridines. The imidazo[4,5-b]pyridine heterocycle is a versatile purine isostere and important ring system which has seen a recent growth in medicinal chemistry application of potential therapeutic benefit; for example in protein kinase inhibitors for the treatment of cancer, inflammatory disease and diabetes. This methodology allows easy access to 2,7- and 2,6-disubstituted derivatives from common intermediates in an approach amenable to the divergent synthesis of analogues and which is applicable to rapid medicinal chemistry exploration of this emerging purine isostere.

Regioselective C2-arylation of imidazo[4,5-b]pyridines
Jonathan Macdonald, Victoria Oldfield, Vassilios Bavetsias and Julian Blagg
DOI: 10.1039/C3OB27477B

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In this HOT paper, Marder, Whiting, Przyborski and co-workers investigate the ability of thiazole-containing small molecules to induce the differentiation of human pluripotent stem cells and their derivatives. Understanding how the structure of molecules relates to their function and biological activity is essential in the development of new analogues with targeted activity. This is especially relevant in mediating developmental processes in mammalian cells and the regulation of stem cell differentiation. This study provides further insight into the complexity of compound design in terms of developing small molecules with specific biological activities to control the development and differentiation of mammalian cells.

Synthesis and applications of 2,4-disubstituted thiazole derivatives as small molecule modulators of cellular development
Garr-Layy Zhou, Daniel M. Tams, Todd B. Marder, Roy Valentine, Andrew Whiting and Stefan A. Przyborski
DOI: 10.1039/C3OB00005B

Free to access for 4 weeks

These articles are HOT as recommended by the referees. And we’ve made them free to access for 4 weeks.

Host–guest complexation driven dynamic supramolecular self-assembly 
Huacheng Zhang, Kim Truc Nguyen, Xing Ma, Hong Yan, Junfei Guo, Liangliang Zhu and Yanli Zhao

Org. Biomol. Chem., 2013, DOI: 10.1039/C2OB27340C

Free to access untill 11th April

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Modular synthesis of polyene side chain analogues of the potent macrolide antibiotic etnangien by a flexible coupling strategy based on hetero-bis-metallated alkenes 

Mario Altendorfer, Aruna Raja, Florenz Sasse, Herbert Irschik and Dirk Menche

Org. Biomol. Chem., 2013, DOI: 10.1039/C2OB26906F

Free to access untill 11th April

 

 

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