Palladium-Catalyzed Acylations: One-Pot Synthesis of Indenones

Abstract

An efficient, one-pot synthesis of substituted indenones was accomplished starting from simple o-iodoketones and aldehydes. [Pd]-catalyzed direct acylation of o-iodoketones with aldehydes was employed as the key step. Subsequent intramolecular aldol condensation afforded the indenones. Notably, a variety of indenones were achieved. Significantly, the natural product neolignan was accomplished in one pot.

An Approach to One‐Pot Regioselective Synthesis of Indenones through Palladium‐Catalyzed Annulation in Water

“…Against this background, we envisioned that it would be feasible to produce indenones with use of water as a green solvent in the presence of simple palladium catalysts and with the support of phase‐transfer catalysts. In continuation of our interests in transition‐metal‐catalyzed domino transformations, we have very recently reported a domino one‐pot synthesis of indenones by way of a Pd‐catalyzed direct acylation and intramolecular aldol condensation sequence . Inspired by these results, we describe here the Pd‐catalyzed one‐pot synthesis of indenones in water as the sole, and green, solvent.…”

“…In continuation of our interests in transition-metal-catalyzed domino transformations, [13] we have very recently reported a domino one-pot synthesis of indenones by way of a Pd-catalyzed direct acylation and intramolecular aldol condensation sequence. [14] Inspired by these results, we describe here the Pd-catalyzed one-pot synthesis of indenones in water as the sole, and green, solvent. Gratifyingly, unlike in most earlier reports, this strategy showed excellent regioselectivity, particularly with unsymmetrical alkylarylacetylenes.…”

Palladium Catalyzed Direct Acylation of Iodo‐Acetanilides/Iodo‐Phenyl Acetates: Domino One‐Pot Synthesis of 2‐Quinolinones

“…Significantly, unlike earlier reports, the reaction was feasible without activating the aldehyde functionality. Consequently, a domino one‐pot synthesis of indenones by using Pd‐catalyzed direct acylation and intramolecular aldol condensation sequence was reported . Inspired by these results, herein, we present a direct coupling of iodoacetanilides/iodophenyl acetates with aldehydes for the synthesis of acylacetanilides/acylphenyl acetates.…”

“…Consequently, a domino one-pot synthesis of indenones by using Pd-catalyzed direct acylation and intramolecular aldol condensation sequence was reported. [10] Inspired by these results, herein, we present a direct coupling of iodoacetanilides/iodophenyl acetates with aldehydes for the synthesis of acylacetanilides/ acylphenyl acetates. In addition, we have demonstrated the one-pot formation of ortho-acylanilines through in-situ hydrolysis of ortho-iodoacetanilides.…”

Heterogeneous Direct Acylation Strategy to Diaryl Ketones and Their Application to 1, 3‐Dihydroisobenzofurans

“…[9b] The method was directing group free and also applied to a good range of synthetic applications. [10] Encouraged by these results, we intended to establish a sustainable protocol enabling the formation of aromatic ketones, using heterogeneous catalysis. Advantages of heterogeneous catalysis are: i) eliminates the metal contamination in products; ii) the easy separation of catalyst from the crude reaction mixture and iii) the catalyst can be reused.…”