A General Palladium‐Catalyzed Carbonylative Synthesis of Chromenones from Salicylic Aldehydes and Benzyl Chlorides

Wu, Xiao‐Feng; Wu, Lipeng; Jackstell, Ralf; Neumann, Helfried; Beller, Matthias

doi:10.1002/chem.201301774

Cited by 41 publications

(9 citation statements)

References 51 publications

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“…[43] Wu et al developed a straightforward synthetic methodology to access several 2-arylcoumarin derivatives via palladium catalyzed three component reaction of salicylic aldehydes with benzyl chloride and gaseous CO using Pd(OAc) 2 /DPPP (1,3-Bis(diphenylphosphino)propane) catalytic system (Scheme 17). [44] The reaction exhibited high functional tolerance under these conditions and afforded a broad range of chromenones in good to excellent yields. The applicability of this approach could be further extended using 2-hydroxyacetophenone as a substrate, which afforded the desired product in 44 % yield.…”

Section: Synthesis Of Chromones Chromanonesmentioning

confidence: 93%

Accessing Medicinally Relevant O‐Benzofused Heterocycles through C−X Activation: Recent Trends

Burke

Moutayakine

2022

Eur J Org Chem

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In this Review, we address the recent advances in the elaboration of medicinally relevant oxygen benzofused heterocycles by palladium and copper catalyzed CÀ X activation of halo arene precursors. This attractive transformation has shown remarkable versatility and efficiency as a synthetic toolkit leading to the construction of numerous scaffolds with high structural diversity in an atom-economical manner. We covered recent examples that considered the application of this strategy using miscellaneous coupling partners and conditions. The haloarene motif has proven to be an exceptional candidate principally due to its availability and cost, and in this review, we showcase relevant and appropriate examples of its use in catalytic reactions leading to medicinally important targets.

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Section: Synthesis Of Chromones Chromanonesmentioning

confidence: 93%

Accessing Medicinally Relevant O‐Benzofused Heterocycles through C−X Activation: Recent Trends

Burke

Moutayakine

2022

Eur J Org Chem

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“…A straightforward procedure for the synthesis of several 3-arylcoumarins via palladium-catalyzed carbonylation of salicylic aldehydes, carbon monoxide and benzyl chlorides, using 1,3-bis(diphenylphosphino)propane (DPPP) as ligand and triethylamine (NEt 3 ) as base, in dioxane, has been developed in good to excellent yields [44]. A highly efficient palladium-catalyzed carbonylative annulation of salicylaldehydes with benzyl chlorides, using N-formylsaccharin-a low cost, solid and easy to handle reactive-avoids the use of the highly toxic carbon monoxide (CO) gas [45].…”

Section: By Reaction With Other Synthonsmentioning

confidence: 99%

3-Phenylcoumarins as a Privileged Scaffold in Medicinal Chemistry: The Landmarks of the Past Decade

2021

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3-Phenylcoumarins are a family of heterocyclic molecules that are widely used in both organic and medicinal chemistry. In this overview, research on this scaffold, since 2010, is included and discussed, focusing on aspects related to its natural origin, synthetic procedures and pharmacological applications. This review paper is based on the most relevant literature related to the role of 3-phenylcoumarins in the design of new drug candidates. The references presented in this review have been collected from multiple electronic databases, including SciFinder, Pubmed and Mendeley.

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“…Concerning the reaction pathway, we proposed a palladium catalyzed oxylcarbonylative reaction and followed an intramolecular condensation. [25] Through palladium-catalyzed carbonylative coupling of 2-aminobenzylamine with aryl bromides, we reported an efficient method for the synthesis of quinazolines (Scheme 19). The reactions followed an aminocarbonylationcondensation-oxidation sequence in a one-pot one-step manner.…”

Section: Scheme 15 Synthesis Of Thiochromenones In Four-component Reactionsmentioning

confidence: 99%

Transition-Metal-Catalyzed Carbonylative Synthesis and Functionalization of Heterocycles

Yin¹,

Wang²,

Wu³

2019

Chin. J. Org. Chem.

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Heterocycles are ubiquitous in natural products, pharmaceuticals, organic materials, and numerous functional molecules. These structural units probably constitute the largest and most varied family of organic compounds. Hence the development of new procedures for heterocycles synthesis has been a hot research topic for over centuries. Among all the new synthetic methods, transition-metal-catalyzed reactions are attractive. Those reactions can formulate complicated heterocycles efficiently from available starting materials under mild conditions and atom economical routes. Among them, transition-metal-catalyzed carbonylation reaction has become an efficient and useful tool in organic synthesis since the first hydroformylation reaction developed by W. Reppe at BASF in the 1930s. Since then impressive progress has been achieved in this area. In nowadays, various types of carbonylation reactions were established. Substrates including aryl halides, olefins, alkynes or simply C-H bond can be activated and produce the corresponding carbonyl-containing compounds smoothly. On the other hand, carbon monoxide was discovered and identified in the 18th century. Since the first applications in industry around 80 years ago, academic and industrial laboratories have explored uses of CO in chemical reactions broadly. However, because of the special physical properties of CO, organic chemists were often reluctant to apply carbonylations frequently in laboratories. Hence, different kinds of CO surrogates were developed and applied in carbonylation reactions, such as metal carbonyl compounds M(CO) x , formates, alcohols, formic acid, aldehyde, biomass and carbon dioxide. Those CO surrogates offer interesting opportunities for carbonylation reactions. This account mainly outlines our progress in the development of transition-metal-catalyzed carbonylative synthesis and functionalization of heterocycles from 2012 to 2018. With copper, palladium, rhodium, ruthenium and iridium as the catalysts and relying on the activation of carbon-halogen and carbon-hydrogen bonds, we are able to synthesis various of heterocycles by using CO gas or CO surrogates as the C1 building blocks.

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A General Palladium‐Catalyzed Carbonylative Synthesis of Chromenones from Salicylic Aldehydes and Benzyl Chlorides

Cited by 41 publications

References 51 publications

Accessing Medicinally Relevant O‐Benzofused Heterocycles through C−X Activation: Recent Trends

Accessing Medicinally Relevant O‐Benzofused Heterocycles through C−X Activation: Recent Trends

3-Phenylcoumarins as a Privileged Scaffold in Medicinal Chemistry: The Landmarks of the Past Decade

Transition-Metal-Catalyzed Carbonylative Synthesis and Functionalization of Heterocycles

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