Palladium‐Catalyzed Carbonylation of 2‐Bromoanilines with 2‐Formylbenzoic Acid and 2‐Halobenzaldehydes: Efficient Synthesis of Functionalized Isoindolinones

Natte, Kishore; Chen, Jianbin; Li, Haoquan; Neumann, Helfried; Beller, Matthias; Wu, Xiao‐Feng

doi:10.1002/chem.201404446

Cited by 33 publications

(7 citation statements)

References 52 publications

(23 reference statements)

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“…After optimization of the reaction conditions, when using Pd(TFA) 2 as the catalyst and NEt 3 as the base, 2-bromobenzaldehyde reacted with 2-bromoaniline under a CO pressure of 8 bar, and a series of functionalized isoindolinones were obtained in good yields. 54 This convenient and highly efficient cascade reaction takes place through a palladium-catalyzed double carbonylation process with a similar mechanism compared to that shown above. To our delight, besides 2-bromobenzaldehyde, 2formylbenzoic acid reacted with 2-bromoaniline under the same conditions and underwent single carbonylation.…”

Section: Account Syn Lettmentioning

confidence: 91%

Recent Achievements in Carbonylation Reactions: A Personal Account

Peng

2016

Synlett

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Section: Account Syn Lettmentioning

confidence: 91%

Recent Achievements in Carbonylation Reactions: A Personal Account

Peng

2016

Synlett

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“…A multi‐component cascade reaction utilizing either carbonylation or double‐carbonylation process of 2‐bromoanilines with 2‐formylbenzoic acid or 2‐halobenzaldehydes generating functionalized isoindolinones was reported by Wu (Scheme 71). [148] In the case of 2‐formylbenzoic acids, the use of 3‐amino‐2‐chloropyridine instead of 2‐bromoanilines resulted in significant drop in the yield but otherwise halide, methyl and acetyl substituents were well tolerated. In the case of 2‐halobenzaldehydes, 2‐iodobenzaldehyde substrates resulted in the highest yields, but still lower than what was obtained with 2‐formylbenzoic acids.…”

Section: Carbonylation: Annulation/cyclizationmentioning

confidence: 99%

Isoindolinone Synthesis via One‐Pot Type Transition Metal Catalyzed C−C Bond Forming Reactions

Savela

Méndez-Gálvez

2021

Chemistry A European J

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Isoindolinone structure is an important privileged scaffold found in al argev ariety of naturallyo ccurring as well as synthetic, biologically and pharmaceutically active compounds. Owing to its crucial role in anumber of applications, the synthetic methodologies for accessingt his heterocyclic skeleton have received significant attentiond uring the past decade. In general, the synthetic strategies can be divided into two categories:F irst, direct utilization of phthalimides or phthalimidines as startingm aterials for the synthesis of isoindolinones;a nd second, construction of the lactam and/or aromatic rings by different catalytic methods, including CÀHa ctivation, cross-coupling,c arbonylation, condensation, addition and formal cycloaddition reactions. Especially in the last mentioned, utilization of transition metal catalysts provides access to ab road range of substituted isoindolinones.H erein, the recent advances (2010-2020) in transition metal catalyzed synthetic methodologies via formation of new CÀCbonds for isoindolinones are reviewed.

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“…Various 2-bromoanilines undergo palladium-catalyzed carbonylation with 2-formylbenzoic acid under a convenient and mild procedure to give good to excellent yields of the corresponding isoindolinones. [24] Scheme 17 Synthesis of phthalazinones and isoindolinones In 2013, our group reported a palladium-catalyzed carbonylative synthesis of coumarins from salicylic aldehydes and benzyl chlorides (Scheme 18). Various coumarins were produced in good to excellent yields.…”

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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Palladium‐Catalyzed Carbonylation of 2‐Bromoanilines with 2‐Formylbenzoic Acid and 2‐Halobenzaldehydes: Efficient Synthesis of Functionalized Isoindolinones

Cited by 33 publications

References 52 publications

Recent Achievements in Carbonylation Reactions: A Personal Account

Recent Achievements in Carbonylation Reactions: A Personal Account

Isoindolinone Synthesis via One‐Pot Type Transition Metal Catalyzed C−C Bond Forming Reactions

Transition-Metal-Catalyzed Carbonylative Synthesis and Functionalization of Heterocycles

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