A new approach for fused isoindolines via hexadehydro-Diels–Alder reaction (HDDA) by Fe(0) catalysis

Vandavasi, Jaya Kishore; Hu, Wan‐Ping; Hsiao, Cheng-Tien; Senadi, Gopal Chandru; Wang, Jhi-Joung

doi:10.1039/c4ra12376j

Cited by 18 publications

(7 citation statements)

References 38 publications

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“…Among those strategies, having one of the C–C double bonds participating in the Diels–Alder reaction replaced by a triple bond, the reaction of the diene with a dienophilic alkyne can afford cyclohexadiene, which process has been called the didehydro-Diels–Alder reaction. Another involvement of alkyne, the combination of 1,3-enyne as the 4π-component with alkyne, results in a cyclic allene adduct, which rapidly rearranges via a [1,5] hydrogen shift to benzene in tetradehydro-Diels–Alder reaction . The cycloaddition between 1,3-diyne and diynophilic alkyne generates a highly oxidized and constrained benzyne via hexadehydro-Diels–Alder reaction, and this versatile intermediate participates in the trapping sequence to develop the structural complexity. − …”

Section: Introductionmentioning

confidence: 99%

Fe(II)/Fe(III)-Catalyzed Intramolecular Didehydro-Diels–Alder Reaction of Styrene-ynes

et al. 2018

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The intramolecular didehydro-Diels-Alder reaction of styrene-ynes was catalyzed by Fe(II) and Fe(III) to produce various naphthalene derivatives under microwave heating conditions. Mechanistic calculations found that the Fe(II) catalyst activates the styrenyl diene in an inverse-electron-demand Diels-Alder reaction, and the consecutive dehydrogenation reaction can be promoted by either Fe(II)-catalyzed direct dehydrogenation or an Fe(III)-catalyzed rearomatization/dehydrogenation pathway.

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Section: Introductionmentioning

confidence: 99%

Fe(II)/Fe(III)-Catalyzed Intramolecular Didehydro-Diels–Alder Reaction of Styrene-ynes

et al. 2018

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“…A related, diiron nonacarbonyl-promoted reaction is shown by the example of 102 to 103 (Figure b) . A number of additional metal-based additives led to the same outcome.…”

Section: Trapping Reactions Leading To Products Having New Types Of A...mentioning

confidence: 83%

Hexadehydro-Diels–Alder Reaction: Benzyne Generation via Cycloisomerization of Tethered Triynes

2021

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The hexadehydro-Diels−Alder (HDDA) reaction is the thermal cyclization of an alkyne and a 1,3-diyne to generate a benzyne intermediate. This is then rapidly trapped, in situ, by a variety of species to yield highly functionalized benzenoid products. In contrast to nearly all other methods of aryne generation, no other reagents are required to produce an HDDA benzyne. The versatile and customizable nature of the process has attracted much attention due not only to its synthetic potential but also because of the fundamental mechanistic insights the studies often afford. The authors have attempted to provide here a comprehensive compilation of publications appearing by mid-2020 that describe experimental results of HDDA reactions. CONTENTS 1. Introduction 2413 1.1. Background: Dehydro-Diels−Alder Reactions 2413 1.2. Earliest Examples of Hexadehydro-Diels− Alder Reactions 2415 1.3. Organization of this Review 2415 2. Diyne-to-Diynophile Substrate Tethers 2415 3. Benzyne Trapping Agents 2416 4. Trapping Reactions Leading to Products Having New Types of Adjacent σ-Bonds at the Benzyne Carbons

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“…In 2014 Wang reported the Fe 2 (CO) 9 ‐catalyzed cycloisomerization of triynols 39 (Scheme ) . Several tricyclic isoindoline derivates 40 were formed in high yields after two hours reaction time.…”

Section: Cycloisomerizations Of Polyunsaturated Organic Compoundsmentioning

confidence: 99%

Fe‐Catalyzed Cycloisomerizations

Teske

Plietker

2017

Israel Journal of Chemistry

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Cycloisomerizations allow the generation of defined molecular complexity starting from structurally simple polyunsaturated starting materials. Iron-based catalysts are newcomers in this field of catalysis that is dominated by catalysts based mainly on palladium, ruthenium, and in particular rhodium. In this review we summarize the most important contributions in this field of catalysis. Apart from "classical" Lewis-acid activations catalysts that possess redox-active ligands are of particular interest since they open new mechanistic pathways and hence new cycloisomerization venues.

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A new approach for fused isoindolines via hexadehydro-Diels–Alder reaction (HDDA) by Fe(0) catalysis

Abstract: A simple method has been developed for the synthesis of fused isoindolines via a cascade HDDA approach catalyzed by Fe2(CO)9.

Cited by 18 publications

References 38 publications

Fe(II)/Fe(III)-Catalyzed Intramolecular Didehydro-Diels–Alder Reaction of Styrene-ynes

Fe(II)/Fe(III)-Catalyzed Intramolecular Didehydro-Diels–Alder Reaction of Styrene-ynes

Hexadehydro-Diels–Alder Reaction: Benzyne Generation via Cycloisomerization of Tethered Triynes

Fe‐Catalyzed Cycloisomerizations

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