The Handy Chemistry Answer Book

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Organic Synthesis: The Disconnection Approach

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Buckyball boron

The stability of the predicted boron cage stems from its unique structural geometry
 Since C₆₀ fullerene’s discovery in 1985 and the subsequent Nobel prize awarded to Robert Curl, Harry Kroto and Richard Smalley in 1996, researchers have been challenging themselves to make similar structures with other elements in the hope of finding exciting alternative nano building blocks.
 http://www.rsc.org/chemistryworld/2014/07/boron-cage-b38-fullerene

B38 Cage: An All-Boron Fullerene Predicted

B38 Cage: An All-Boron Fullerene Predicted

Hydrophobic Catalysts

Hydrophobic Catalysts

Tetrahedron. Author manuscript; available in PMC Feb 4, 2013.

Published in final edited form as:

Tetrahedron. Feb 4, 2012; 68(5): 1359–1366.

Published online Dec 13, 2011. doi:  10.1016/j.tet.2011.12.013

PMCID: PMC3358821

NIHMSID: NIHMS344972

Acid-Facilitated Debenzylation of N-Boc, N-Benzyl Double Protected 2-Aminopyridinomethylpyrrolidine Derivatives

Haitao Ji,^1,2 Qing Jing,¹ Jinwen Huang,^1,3 and Richard B. Silverman^1,*

¹Departments of Chemistry and Molecular Biosciences, Chemistry of Life Processes Institute, and Center for Molecular Innovation and Drug Discovery, Northwestern University, Evanston, Illinois 60208-3113

^*Correspondence to the Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208-3113, Phone: 847-491-5653, Email: ude.nretsewhtron.mehc@namgA

²Current address: Department of Chemistry, University of Utah, Salt Lake City, UT 84112-0850

³Current address: Shanghai HotMed Sciences Co., Ltd., Shanghai Zhangjiang Hi-Tech, Park,211-214 NO.518, Bibo Road, Shanghai, China

Author information ► Copyright and License information ►

Copyright notice and Disclaimer

Publisher's Disclaimer

The publisher's final edited version of this article is available at Tetrahedron

Go to:

 http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3358821/#R2   click here

Abstract

2-Aminopyridinomethyl pyrrolidines represent a class of highly potent and selective neuronal nitric oxide synthase inhibitors. Conditions for a Mitsunobu reaction of a naphthol and a hindered secondary alcohol were optimized to give good to excellent yields. A key step in the synthesis of these inhibitors is the deprotection of the benzyl group from the N-Boc and N-Bn double protected 2-aminopyridine ring at a late stage of the synthesis, which has been proven difficult in our previous syntheses. Acetic acid was found to facilitate the N-Bn deprotection.

Keywords: 2-Aminopyridinomethyl pyrrolidines, Mitsunobu reaction, N-Benzyl deprotection, Palladium-catalyzed hydrogenation

Minisci reactions: Versatile CH-functionalizations for medicinal chemists « New Drug Approvals

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A Midas Touch on Azobenzene

A Midas Touch on Azobenzene

A novel azobenzene forms non-metallic crystals with long-lasting gold color
Read more

One Method, Four Enantiomers

One Method, Four Enantiomers

Four enantiomers of beta-lactams produced from a single starting material
Read more

Solvent-Free Organocatalytic Michael Reactions

Solvent-Free Organocatalytic Michael Reactions

Chiral thiohydantoins derived from natural α-amino acids are the key catalysts
Read more

Ionic Liquid Solubilizes Fullerene in Water

Ionic Liquid Solubilizes Fullerene in Water

Modeling shows imidazolium ionic liquid facilitates the dispersion of C60 in water by forming solute pair
Read more

Titania-catalysed oxidative dehydrogenation of ethyl lactate: effective yet selective free-radical oxidation

Titania-catalysed oxidative dehydrogenation of ethyl lactate: effective yet selective free-radical oxidation

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Titania-catalysed oxidative dehydrogenation of ethyl lactate: effective yet selective free-radical oxidation

Titania-catalysed oxidative dehydrogenation of ethyl lactate: effective yet selective free-radical oxidation

http://pubs.rsc.org/en/Content/ArticleLanding/2014/GC/C4GC00191E?utm_source=feedburner&utm_medium=feed&utm_campaign=Feed%3A+rss%2FGC+%28RSC+-+Green+Chem.+latest+articles%29#!divAbstract

Green Chem., 2014, 16,3358-3363
DOI: 10.1039/C4GC00191E, Paper

 Open Access

  This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.

Enrique V. Ramos-Fernandez, Norbert J. Geels, N. Raveendran Shiju, Gadi Rothenberg
Set them free? Combining a solid catalyst and a solid free-radical scavenger, gives a free-radical oxidation that gives high selectivity even at high concentrations.


We research here the catalytic oxidative dehydrogenation of ethyl lactate, as an alternative route to ethyl pyruvate. Testing various solid catalysts (Fe₂O₃, TiO₂, V₂O₅/MgO–Al₂O₃, ZrO₂, CeO₂ and ZnO), we find that simple and inexpensive TiO₂ efficiently catalyses this reaction under mild conditions. Furthermore, molecular oxygen was used as the terminal oxidant. Importantly, this reaction runs well also using inexpensive commercial solvent mixtures. Both the desired reaction and the by-products formation follow a free-radical mechanism. Remarkably, adding activated carbon, a solid radical scavenger, hardly affects the catalytic activity, but enhances the product selectivity. This is because this solid radical scavenger hampers the formation of undesired products in solution, without suppressing the oxidation at the catalyst surface.