Selective formation of phthalimides from amines, aldehydes and CO by Pd-catalyzed oxidative C–H aminocarbonylation

Shi, Renyi; Liao, Fan; Niu, Huiying; Lei, Aiwen

doi:10.1039/c8qo00282g

Cited by 11 publications

(5 citation statements)

References 89 publications

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“…The in situ produced imines could be regarded as a directing group. In 2018, Jiang 56 and our group 57 reported the Pdcatalyzed C(sp 2 )-H carbonylation to generate phthalimides (Scheme 15). In these works, the imines could be obtained via the condensation between amines with aldehydes, which can be regard as the directing group.…”

Section: ■ Brief Introductionmentioning

confidence: 99%

An Update on Oxidative C–H Carbonylation with CO

Liu

Chen

et al. 2022

ACS Catal.

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Carbonyl derivatives widely exist in pharmaceuticals, agricultural chemicals, materials, and natural products. Developing novel, efficient, and green carbonylation methods represent one of the hottest research topics in organic synthesis, not only for academics but also for the chemical industry. Carbon monoxide (CO) turns out to be the most ideal carbonyl source because of its 100% atomic efficiency and low price. Meanwhile, compared with “classical” cross-coupling between nucleophiles and electrophiles, oxidative cross-coupling, which uses nucleophiles as reactants under oxidation conditions, has received increasing attention during the past two decades. Among oxidative carbonylation, the C–H functionalization/carbonylation is undoubtedly one of the most atom- and step-economical methods. Due to its great potential in green synthesis, this field has grown vigorously over the past decade, and many strategies have been developed, including transition metal catalysis, photoredox catalysis, electrochemical protocol, and so on. Since our last review of oxidative carbonylation in 2011, the C–H bond carbonylation has attracted continuous attention and undergone extensive development. Therefore, it is time to update this important field.

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Section: ■ Brief Introductionmentioning

confidence: 99%

An Update on Oxidative C–H Carbonylation with CO

Liu

Chen

et al. 2022

ACS Catal.

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“…Phthalimide derivatives are promising pharmacologically active compounds, commonly used as analgesic, antimicrobial, anti‐inflammatory, antitumor, and anticonvulsant drugs. [ 144 ] In this context, Lei [ 145 ] reported a palladium‐catalyzed oxidative C—H carbonylation of aryl aldehydes, under 1 bar CO pressure, using aniline derivatives as nucleophiles, a Pd(II)/dppf as catalyst and Cu(OPiv) 2 (Piv = pivaloyl) as oxidant (Scheme 81). With this protocol, the authors managed to prepare a large family of biologically relevant phthalimide compounds, in moderate to good yields (45%—99%), compatible with diverse functional groups.…”

Section: Synthesis Of Fine Chemicals Using Comentioning

confidence: 99%

Carbon Monoxide as C1 Building Block in Fine Chemical Synthesis^†

Carrilho,

Calvete,

Mikle

et al. 2023

Chin. J. Chem.

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Carbon monoxide (CO) has become one of the most relevant and versatile renewable C1 building blocks for chemical synthesis, especially in the fine chemicals industry, due to the development of efficient and selective catalysts for its activation. In this review, we present a comprehensive critical analysis of the last 10 years literature on the use of CO as a renewable feedstock for fine chemicals production. The review is organized by type of catalytic reaction, namely alkene and alkyne carbonylation, hydroformylation, carbonylation of aryl halides, carbonylative cross‐coupling and C–H carbonylation. Notable examples of the synthesis of relevant building blocks and/or known pharmaceuticals are highlighted. Emphasis is placed on examples of utilizing CO as the C1 building block in one or more catalytic steps. The catalyst used and the reaction conditions are consistently presented throughout all of the examples.This article is protected by copyright. All rights reserved.

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“…Lei demonstrated the synthesis of substituted phthalimides from aldehydes via a transient dual palladium/copper catalysed carbonylative strategy (Scheme 7b). 25 This method proceeds by a Pd II /Pd 0 catalytic cycle, with copper pivalate as a catalytic reoxidant and oxygen as the terminal oxidant. Several substituted benzaldehydes were reactive but lower yields were observed with systems bearing electron-withdrawing groups.…”

Section: Organic and Biomolecular Chemistry Reviewmentioning

confidence: 99%