Room temperature palladium catalysed coupling of acyl chlorides with terminal alkynes

Abstract

Conditions are reported for the facile, high-yielding coupling of acyl chlorides with terminal alkynes in a reaction involving palladium and copper iodide; the reaction is tolerant of a wide variety of acyl chlorides and terminal alkynes and provides a convenient one-pot route to acetylenic ketones.

Reaction of Frustrated Lewis Pairs with Conjugated Ynones‐Selective Hydrogenation of the Carbon–Carbon Triple Bond

“…Treatment of the ynones 3 a and 3 c, respectively, with B(C 6 F 5 ) 3 gave the respective Lewis acid adducts (9 a, 9 c [9] ]. Compound 9 a was characterized by X-ray diffraction (see Figure 3: B1-O1 1.570(3), O1-C2…”

Facile Doping and Work‐Function Modification of Few‐Layer Graphene Using Molecular Oxidants and Reductants

“…1 using the peak potentials for reduction of the corresponding monomer cations obtained by cyclic voltammetry in THF / 0.1 M Bu4NPF6 using ferrocene as an internal reference (scan rate = 50 mV s -1 , hardware as for Mo complexes) and values of GDiss obtained from DFT calculations as described in ref [52]. [82] (1.3 g, 6.3 mmol) was added by syringe to a deoxygenated suspension of (NEt4 + ) spectroscopy. The color of the solution turned from red-brown to green to blue, and brown gas was evolved.…”

The thermoregulated ligand–palladium‐catalyzed carbonylative Sonogashira coupling of aryl iodides with terminal alkynes in water

“…The reactions between substituted phenylacetylenes such as 4-methylphenylacetylene and various aryl iodides also proceed effectively to yield 78-86% of carbonylative products ( Table 2, entries 10-14). The reactions of aliphatic alkynes are found to be slower than those of arylacetylenes ( Table 2, entries [15][16][17]. Aryl bromides do not show any conversion, even when harsher conditions are applied (CO at 1 MPa; 10 h).…”

“…[12][13][14][15] A common route to alkynones involves the transition-metal-catalyzed cross-coupling reactions of acid chlorides with terminal alkynes. [16][17][18][19][20] However, the stability and functional group compatibility of acid chlorides have limited the applications of this methodology. Alternatively, the three-component coupling reaction of terminal alkynes, carbon monoxide and aryl halides, generally known as the carbonylative Sonogashira reaction, [21] has become one of the most straightforward and convenient processes for the synthesis of alkynones.…”