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A mind-bending, one-step synthesis of 5-ethyl-2-methylpyridine (from Earth, Water, Air and Fire)

By drfreddy On February 12th, 2011 · 3 Comments

Don’t get me wrong, I love Organic Syntheses, but sometimes the lack of a proper rationale is frustrating. In all likelihood, we will never know how this reaction was conceived. No, it is not a misprint, I have triple-checked it.

Org. Synth. 1963, Coll. Vol. 4, 451-453. (Available here.)

How do you […]

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Methoxy is foxy — Recent advances with Ni(COD)2

By drfreddy On February 12th, 2011 · Leave a Comment

Aromatic methoxy-groups are peachy. Synthetic chemists can use them as directing groups for regio-selective lithiations, Friedel-Crafts acylations or halogenations, to name a few basic concepts. Medicinal chemists seem to dig methoxy-groups too, because they can pick up new hydrogen-bond interactions, and increase steric bulkiness, pKa and log P.

Yeah… we all love the good ol’ […]

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Proposal: Journal of Failed Reactions

By drfreddy On February 10th, 2011 · 7 Comments

Someone should start up a new journal entitled the Journal of Failed Reactions. I’m serious. The contemporary primary literature is a collection of success stories. Fine. This is how things are supposed to be.

But—every chemist with experience in the field of organic synthesis knows that the vast majority of the reactions we attempt are, […]

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Awesome functional group transformation #2

By drfreddy On January 25th, 2011 · Leave a Comment

You have the aryl bromide. You need the corresponding aniline. Buchwald-Hartwig isn’t working.

Been there. Done that. Got the t-shirt.

What to do? Check this out! A catalytic Ullman amination. No need for stochiometric amounts of copper. Ligand and solvent free. Table 3, entry 1, for instance.

JOC 2011, Article ASAP (Available here.)

The […]

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Legal Highs: The Dark Side of Medicinal Chemistry

By drfreddy On January 6th, 2011 · Leave a Comment

Professor David Nichols, one of the World’s greatest authorities on novel psychoactive compounds, has just published an amazingly clear and honest column in the latest issue of Nature (doi:10.1038/469007a). Grab it here. It is a must-read.

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“Hidden gems” in Chemistry Letters

By drfreddy On December 21st, 2010 · Leave a Comment

I’d say Jun Shi, a graduate student in Baran’s group at The Scripps Research Institute, was pretty well prepared for that internal group meeting that apparently took place on April 17, 2010. Judging by these slides, which I accidently just stumbled upon via Google, I’d say she was very well prerpared. Amazing work—Thank you!

[…]

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The correct form of uncorrect is incorrect!

By drfreddy On December 12th, 2010 · 1 Comment

I think the most tedious part of preparing a manuscript for publication is the proof-reading. It’s a dirty job, but someone’s gotta do it. If not done properly, you risk world-class typos like this to slip through.

J. Organomet. Chem. 2005, 690, 4252-4257. (Available here.)

P.S. For the record, the generic phrase is […]

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Awesome functional group transformation #1

By drfreddy On December 4th, 2010 · Leave a Comment

I have a weak spot for new, SIMPLE and potentially powerful transformations.

I am certainly not alone, and I am certainly not the first to confess to this preference. Some call it Occam’s razor, others the KISS principle (Keep it simple, stupid). The origin is tracable even to Aristotle (who lived some 3-400 years […]

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I love this journal

By drfreddy On November 22nd, 2010 · Leave a Comment

Not that I have stumbled upon it in the physical world, read it online, or ever seen single a reference to it. Merely because of its name:

Drugs of the Future

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Two people who clearly underestimated their personal impact factor

By drfreddy On November 12th, 2010 · 1 Comment

In hindsight, these two guys should perhaps have considered submitting their manuscripts to journals with a… ahem… slightly higher impact factior. Then again, how could they possibly have predicted that they would end up Name Reactions?

S. O. Lawesson et al.; Bulletin des Sociétés Chimiques Belges 1978, 87, 223-228. (No DOI available, not available online.)

[…]

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