A recent report by Cheng, Jia, and Kuang (1) of Tongji University is a useful – and pleasantly straightforward- addition to the methods available for alkyne synthesis. The Terminal Alkyne Synthesis of Kuang et Al. (1) The alkyne functionality is crucial to modern methods (Sonogashira coupling, ’Click’ chemistry, methathesis reactions) and terminal alkynes can be prepared in a handful of ways. These include the Colvin […]
Alkyl halides are a most fundamental functional group and are useful in many reactions. Typically alkyl chlorides are derived from alkanols, and Dudley Snyder of Pennsylvania State reported an attractive synthesis which uses a ‘DMSO-activated’ TMSCl intermediate (1) An example from the Dudley paper (1) There are some advantages to Snyder’s technique relative to the established methods, such […]
Li, Han, and coworkers of the Dalian Institute of Chemical Physics have reported an isocoumarin synthesis that proceeds through a nucleopalladative-oxidation olefination pathway (1). Li, Han, and coworkers report the oxidative coupling of olefins and t-butyl 2-alkynylbenzoates to produce isocoumarins (1) The isocoumarin products formed can possess some degree of complexity, based on the initial […]
A recent report (1) from workers at Chonnam National University (Gwangju, Korea) describes a benzimidazole synthesis which: produces good product yields (40-98%, for about 30 examples) and proceeds in one pot from three readily available components: sodium azide, an aldehyde, and 2-haloanilines shows good functional group tolerance(nitro-, ester-, chloro-, and various heterocyclic functionalities on the aldehyde or haloaniline component). […]
The work of Lee, Song and coworkers (1) provides an versatile route to symmetrical and unsymmetrical diarylalkynes. Their method is complementary to the powerful Sonagashira coupling of aryl halides and alkynes, and offers an alternative to the established ways to make diarylalkynes.
Our second set of evaluations was guided by the work of Bahrami, Khodaei, and coworkers (1). Their sulfide oxidation method seemed attractive for our purposes, and there were several examples given which were structurally similar to our target compounds. The oxidation procedure of Bahrami, Khodaei and coworkers (1) Some features of this method: fast reaction […]
The sulfide oxidation procedure of Page and coworkers (1) Our first trial was based on the work of Page and coworkers at the University of Liverpool (1). A first look at this procedure suggested it would be simple to implement in the lab and could be used to produce preparative quantities of the sulfoxide we required. Features […]
The lab recently required some small (5-10g) samples of some simple dialkyl sulfoxides. This led us to investigate dialkylsulfide oxidation procedures capable of producing these compounds selectively, with minimal overoxidation to sulfone byproducts. There are, of course, many ways to go about this reaction. Hydrogen peroxide in the presence of a Lewis acid (1), Caro’s […]