Issue 31 September 2009

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Fe Catalysis – Fact or Fiction?

Iron catalysis has been a growing area of interest in recent years helped by the low cost and toxicity of most iron catalysts particularly when compared to Pd, Ru, Rh etc. However a recent paper1 from Carsten Bolm and Steven Buchwald casts doubt on iron’s perceived role in some FeCl3 catalysed aryl coupling reactions between aryl iodides and phenols, thiophenols and imidazoles.

Birch Reduction with Na, K on Silica Gel

Alkali metals in silica gel (M-SG) have been developed at Michigan State University as dry, free flowing powders which can replace dissolving metal conditions, typically requiring liquid ammonia, for carrying out reductions and other transformations.

Aromatic Fluorination

ArOSO2CF3 + CsF → ArF

A recent Science paper (published on the web) from Stephen Buchwald and his group describes a system for generating aromatic fluorides by palladium catalysed displacement of triflates using cesium fluoride.

Efficient Synthesis of Oseltamivir Phosphate, the Active Ingredient of Tamiflu

This recent report (Angew Chem Int Ed 2009, 48, 5760-5762) from Roche process R&D describes a new and scalable synthesis starting from shikimic acid.

Alkaline Earth Metals in Synthesis

When was the last time you used a calcium, magnesium, strontium or barium catalyst in organic synthesis? I suspect many have never used one at all. Well a recent article (Angew Chem Int Ed, 2009, 48, 5790) by Uli Kazmaier reviews recent work in the area.

Books
Two New Books on Crystallisation and Polymorphism ...
Topical Tips

Alternatives to Acetonitrile as a Solvent for HPLC Analysis

Fluoride Free Cleavage of Triisopropylsilyl (TIPS) Protecting Groups

... and finally ...
... The Merck study on hplc solvents included in this newsletter suggests ethanol as a good alternative. We'll certainly drink to that.