ChemInform Abstract: VERBINDUNGEN MIT KONJUGIERTEN AETHYLEN‐ UND ACETYLEN‐GRUPPEN 3. MITT. SYNTH. VON KETONEN MIT ALPHA‐ACETYLENGRUPPIERUNG DURCH KONDENSATION VON LI‐ACETYLIDEN MIT BENZYLCYANID

Abstract

Die Kondensation von Benzoylcyanid (I) mit den Li‐Derivaten (II) in Äther bei ‐70°C liefert die Ketone (III) mit einer α‐Acetylengruppierung.

A copper- and solvent-free coupling of acid chlorides with terminal alkynes catalyzed by a polystyrene-supported palladium(0) complex under aerobic conditions

“…1 They have mainly been used for the preparation of important biologically active heterocycles. 2 Their preparation typically involves the reaction of alkynyl organometallic reagents of silver, 3 copper, 4 sodium, 5 lithium, 6 cadmium, 7 zinc, 8 silicon, 9 or tin 10 with acid chlorides. The direct coupling of alkynyl palladium reagents with acid chlorides is an important method for the preparation of alkynyl ketones.…”

Highly Efficient Copper- and Palladium-Free One-Pot Coupling of Alkynes with Sodium Carboxylate Salts Using Cyanuric and Magnesium Chlorides

“…9 From a synthetic point of view, the use of very toxic CO as well as expensive palladium catalysts and oxidizing reagents, has limited the applicability of these approaches. Alternative methods to access ynones are the reaction of alkynyl organometallic reagents such as silver, 10 copper, 1b,11 sodium, 12 lithium, 13 cadmium, 14 zinc, 15 indium, 4b silicon, 16 thallium, 17 or tin 18 with acid chlorides. The reaction of alkynes with acid chlorides in the presence of metal salts such as copper(I) salts 19 and zinc bromide 20 have also been reported.…”

“…Moreover, the coupling reaction of phenyl acetylene with aliphatic sodium carboxylate salts furnished the desired 1 8b,c,f,g,20 1 9 5 2 8c,20a 1 9 2 3 6b,8c,20a 1 9 0 4 6b,8g,20b 2 9 1 5 8g,20 2 9 0 product in good yields (Table 4, entries [13][14][15]. To further evaluate the utility of this coupling reaction, the coupling of aliphatic terminal alkynes with sodium carboxylate salts were also evaluated.…”

Carbonylative Sonogashira Coupling of Terminal Alkynes with Aqueous Ammonia

“…Synthesis of α,β-alkynyl ketones attracts considerable interest because of their appearance in a wide variety of biologically active molecules and their key synthetic intermediates . A common route to prepare the compounds involves the reaction of alkynyl organometallic reagents such as silver, copper, , sodium, lithium, cadmium, zinc, silicon, and tin with acid chlorides. An alternative synthetic method for α,β-alkynyl ketones is the transition metal-catalyzed coupling of terminal alkynes or the metalated derivatives with organic halides in the presence of carbon monoxide.…”