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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

A Nitrogen Version of the Baeyer-Villiger Oxidation? We’ve Been Expecting you Mr Bond

Perhaps the best-known ring-expansion reaction is the Baeyer-Villiger oxidation, first reported in 1899- not surprisingly by Adolf von Bayer and Victor Villiger. As we’re all aware, reaction of a carbonyl with a peracid generates a Criegee-type intermediate that undergoes rate-limiting concerted rearrangement to form an ester or lactone. The migration order is substituent dependant, with

Boron Joins the Nitro-Circus

The first electrophilc aromatic substitution reaction you were taught as an undergraduate was almost certainly nitration.1 Nitration and subsequent reduction of the aryl nitro group to an aniline via high temperature metal catalysed hydrogenation remains an important industrial process. The reduction has many flavours- both in terms of the substitution pattern on the aryl (and

Thianthrenium is Back – and this Time its Vinyl!

The ability to handle gaseous reagents presents a number of challenges for synthetic chemists. The problem becomes particularly acute when scaling up biphasic (liquid/gas) or even triphasic (gas/liquid/solid) systems due to limiting mass transfer effects. Pressure vessels or autoclaves are also not always practical and easy to come by. A practical solution to this (if

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