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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

Grease is the word…

Many years ago, I heard an anecdote regarding a fortuitous discovery in the Sharpless lab. A graduate student had been awarded their PhD and the group were celebrating in the lab with bottles of red wine (I know- but they were different times). Someone in the group-who had obviously consumed a sufficient quantity of the

A couple of interesting papers from Angewandte Chemie

1. Using an approved drug as a diazomethane surrogate1 A recent paper published in Angewandte Chemie describes the use of Temozolomide (TMZ) as a solid weighable diazomethane surrogate. TMZ is an approved drug and is the standout treatment for gliobastoma.  It is stable weighable solid, with reasonable water solubility.  Under physiological conditions , pH 7.4,

Intermolecular reductive C-N cross coupling of nitroarenes and boronic acids by P(III) / P(V)=O catalysis

When approaching the synthesis of an aryl- or heteroaryl- amine most people would turn to a suitable transition metal (Pd, Cu or Ni) catalysed C-N cross-coupling reaction- most likely a Buchwald-Hartwig reaction, or, if this has limited success, Ullmann or Chan-Evans-Lam couplings.1 Photoredox approaches using aryloxy amides as a source of amidyl radicals began a trend

Cyanomethylene trimethylphosphorane (CMMP)- a safer reagent for Mitsunobu couplings

The Mitsunobu reaction is a powerful coupling method for alkylation of various nucleophiles (H-A) with alcohols (R-OH).[1] The classical conditions use a redox system comprising of an azodicarboxylate (such as diethylaziodicarboxylate, DEAD) and a phosphine (normally triphenylphosphine, TPP). The alcohol is essentially activated in situ and coupling occurs with the generation of the phosphine oxide

Synthesis of biaryls without using heavy metals- the photosplicing approach

Medicinal chemists love introducing aromatic rings into their pharmacophores. These flat rings make important lipophilic and pi-stacking interactions with proteins and are good synthetic handles for attaching functionality to reach and bind to all the nooks and crannies of an active site. With the advent of cross-coupling chemistry and the simplicity and efficiency of transition

Suzuki-Miyaura Cross-Coupling of Amides and Esters

The Suzuki-Miyaura cross coupling reaction has been widely used in industry for C-C bond formation but has not successfully been applied to unactivated substrates such as amides and esters, in which the C-N and C-O bonds are cleaved. This recent report from scientists in Wroclaw (Poland), Beijing and New Jersey gets around the normally slow

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