An economic and efficient tetrahydrofuranylation of alcohols, imines and alkynes

Stereoselective Synthesis of α‐Alkylidene β‐Oxo Amides by Palladium‐Catalyzed Carbonylation

“…On the basis of our previous studies of the carbonylative coupling of allylic halides with imines, [4][5][6][7][8] we hypothesize that the first step of the reaction for the cases described herein should be the formation of a dicarbonyl-palladium intermediate A, which is subsequently involved in the coupling with the aromatic imine to afford a β-lactam ring (B, Scheme 3). On the basis of our previous studies of the carbonylative coupling of allylic halides with imines, [4][5][6][7][8] we hypothesize that the first step of the reaction for the cases described herein should be the formation of a dicarbonyl-palladium intermediate A, which is subsequently involved in the coupling with the aromatic imine to afford a β-lactam ring (B, Scheme 3).…”

“…[2] Palladium-catalyzed carbonylations are widely used not only in academic laboratories but also in industrial ones, as the high efficiency of the method allows its employment on a large scale. Particularly, we have reported that a wide range of allyl and benzyl halides generate an acylpalladium halide (A) as a key reactive intermediate [ substituted amides (Scheme 1, path d) [7] and conjugated acetylenic ketones (Scheme 1, path e) [8] can be obtained from primary or secondary amines and aryl-or alkylacetylenes, respectively. Particularly, we have reported that a wide range of allyl and benzyl halides generate an acylpalladium halide (A) as a key reactive intermediate [ substituted amides (Scheme 1, path d) [7] and conjugated acetylenic ketones (Scheme 1, path e) [8] can be obtained from primary or secondary amines and aryl-or alkylacetylenes, respectively.…”

“…[3] Recently, we have performed several carbonylation reactions involving palladium catalysis. Particularly, we have reported that a wide range of allyl and benzyl halides generate an acylpalladium halide (A) as a key reactive intermediate substituted amides (Scheme 1, path d) [7] and conjugated acetylenic ketones (Scheme 1, path e) [8] can be obtained from primary or secondary amines and aryl-or alkylacetylenes, respectively.…”

Heterocycle Synthesis through Pd‐Catalyzed Carbonylative Coupling

“…The time interval considered comprises the original articles published in the literature during the last four years, since previous studies have already been reviewed in an excellent way. [6] and 2) generated in situ, under a carbon monoxide pressure of 27 atm, by means of Pd-catalyzed carbonylation of the corresponding allyl and benzyl halides [7][8][9][10][11] or other unsaturated halides such as α-chloroketones [12] (Scheme 1). The carbonylative coupling of such key reactive intermediates was investigated showing its great synthetic utility for the preparation a variety of carbonyl-containing acyclic and cyclic organic compounds.…”

“…The carbonylative coupling of such key reactive intermediates was investigated showing its great synthetic utility for the preparation a variety of carbonyl-containing acyclic and cyclic organic compounds. [7][8][9][10][11][12] Scheme 1. Acylpalladium intermediates generated in situ through a Pd-catalyzed carbonylation reaction of unsaturated chlorides.…”