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Now You See Me, Now You Don’t- a Judicious Work-Around for Over-Bromination at Benzylic Carbon

One of the most challenging reactions we carry out as synthetic chemists is bromination of a benzylic carbon- the so called Wohl-Ziegler reaction.1 It’s a seemingly simple transformation – not particularly difficult to perform- and potentially very useful. In fact it’s a little too easy. Just add NBS and a radical initiator to an aryl

Using Electrochemistry to Make Carbon-Carbon Bond Formation More Sustainable

Finding generally applicable, more sustainable, scalable methods to construct C-C bonds via cross-coupling is likely to be one of the major challenges that process chemists will face over the next decade. At the moment chemists overwhelmingly rely on pre-formed nucleophilic organometallics (such as Grignard, organozinc and organoboron reagents) in C-C couplings with an electrophile (such

Accelerating Reaction Development through Open-Source HPLC Data Analysis

Acquisition and processing of analytical HPLC data is often the main bottleneck when performing automated data-rich or high-throughput experimentation. Even though it was over 20 years ago, I well remember spending most of each day running, processing and compiling HPLC data when using an automated reaction platform to run 4 data-rich time course experiments in

Light, Camera, Action- Photoinduced Oxygen Transfer using Nitroarenes to Cleave Alkenes

When one thinks about the chemistry of alkenes, oxidative cleavage via ozonolysis will be close to the top of the list. Certainly in the top 5. Discovered by the Swiss chemist Friedrich Schönbein in 1839, this reaction remains -both academically and industrially- a highly efficient, sustainable method for introducing oxygen into both simple feedstock materials

PerFected Cubane

In the spring of 1940, John Archibald Wheeler, eminent theoretical physicist, called up his then PhD student, Richard Feynman (generally regarded as the most famous modern-age physicist) and said “Feynman- perhaps there’s only one electron in the Universe” a single entity moving backwards and forwards in time. If true it would be one hard working

Something Unique or Methyl, Butyl, Futile? Born again Boron

I can’t begin to count the number of aryl boronic acids I’ve made and/or worked with over the years. These versatile intermediates will forever be part of the synthetic organic chemist’s toolbox. You would be hard pushed to find an organic chemist that hasn’t run a Suzuki- Miyaura cross coupling reaction at some stage in

Rhodium takes Frigid Phenol to New Heights

Phenols and anilines are two of the most important building blocks in industrial chemical manufacturing. Any process capable of converting one into the other is going to generate a lot of interest, and a paper by Shi and co-workers does just that.1 Direct conversion of an aniline to a phenol is a relatively straightforward transformation

Metal Hydride? NO Protection, NO Problem and NO-Where to Hide

Process chemists at Genentech recently published their work on development of a kilo-scale synthesis of JAK-1 inhibitor- GDC-4379 (Figure 1).1The central heterocyclic core of the molecule consists of a 4-aminopyrazole moiety (elaborated as the pyrazolopyrimidene amide- presumably the inhibitor hinge binding fragment in the kinase active site) with an additional aryl substituent at C-3 and

A Scalable Alternative to Chromium-Mediated Allylic Oxidation

Oxidation of allylic alcohols to enones, although on paper a simple reaction, usually requires insidiously toxic metals or metalloids such as chromium and selenium or hazardous peroxy- reagents.1 Scale-up of these methods remains particularly challenging. A team from GSK found themselves in precisely this position when developing a synthetic route to a steroid-derived HIV maturation

Me-Me-Me-Me-Me- Not just a Narcissistic Opera Singer!

The importance of methylation in the discovery and development of bio-active small molecules is well known. I presented a webinar a couple of years ago on the “The magic methyl in medicinal chemistry,” demonstrating the unique properties of this, the simplest functional group.1 I also reviewed the state of the art in synthetic approaches to

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