A Practical Method for the Synthesis of 2-Alkynylpropenals

Abstract

A general method for the preparation of 2-alkynyl acroleins is described beginning with vinyl iodide 5 and involving a combination of Sonogashira coupling and Dess-Martin oxidation. Critical to the success of this approach is the use of a special workup procedure for the oxidation step. The resultant enynals participate in a variety of addition reactions including aldol condensations and reactions with organolithium compounds.

Transition metals in organic synthesis: Highlights for the year 2005

“…The palladium-catalyzed coupling between terminal alkynes and aryl and alkenyl halides or triflates, usually called the Sonogashira coupling, was one of the more frequently utilized carbon-carbon coupling reaction [297][298][299]. Silver-acetylides were formed in situ and are indicated as intermediates in palladium-silver catalyzed Sonogashira couplings [300].…”

Chemical Space Exploration of Oxetanes

“…Then a Brown hydroboration reaction was carried out followed by oxidation of the borate, in which the alkene was converted into the primary alcohol 8, using hydrogen peroxide in basic conditions [25,26]. The alcohol 8 was then oxidized to the aldehyde 9 using Dess-Martin periodinane [27] and subsequently converted into the diol 10 and oxetane 11 employing the same reactions mentioned before (Scheme 2). In the case of (5-chloro-2,3-dihydro-1H-indene-1,1-diyl)dimethanol, as the Corey-Chaykovsky epoxidation reaction did not work, the 5-chloro-indanone 6 was converted in compound 7 through a Wittig reaction [24].…”

3D designed and printed chemical generators for on demand reagent synthesis

“…Compared to its predecessor, 2-iodoxybenzoic acid (IBX), DMP is more stable and typically shows higher reactivity and much better solubility in organic solvents due to the presence of acetoxy groups 37 . It has been demonstrated that compared to other common oxidants based on chromium salts or sulfur ylides, DMP often requires milder conditions thus enabling conversion of challenging and valuable substrates 38,39 . DMP is easily prepared from IBX (Fig.…”