Recent Advances in Alkenyl sp² C–H and C–F Bond Functionalizations: Scope, Mechanism, and Applications

Chemical Reviews, Год журнала: 2022, Номер 122(24), С. 17479 - 17646

Опубликована: Окт. 14, 2022

Alkenes and their derivatives are featured widely in a variety of natural products, pharmaceuticals, advanced materials. Significant efforts have been made toward the development new practical methods to access this important class compounds by selectively activating alkenyl C(sp2)–H bonds recent years. In comprehensive review, we describe state-of-the-art strategies for direct functionalization sp2 C–H C–F until June 2022. Moreover, metal-free, photoredox, electrochemical also covered. For clarity, review has divided into two parts; first part focuses on currently available using different alkene as starting materials, second describes bond easily accessible gem-difluoroalkenes material. This includes scope, limitations, mechanistic studies, stereoselective control (using directing groups well metal-migration strategies), applications complex molecule synthesis where appropriate. Overall, aims document considerable advancements, current status, emerging work critically summarizing contributions researchers working fascinating area is expected stimulate novel, innovative, broadly applicable functionalizations coming

Язык: Английский

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Recent Advances in Reactions Using Enaminone in Water or Aqueous Medium

Advanced Synthesis & Catalysis, Год журнала: 2022, Номер 364(9), С. 1508 - 1521

Опубликована: Апрель 8, 2022

Abstract Enaminones have in the past decade received renewed interest organic synthesis by acting as highly versatile building blocks. Particularly, featured amino and carbonyl group enaminone structure endow them with ability of tolerating water via hydrogen bonding effect. Thus, designing synthetic methods aqueous medium enaminones main blocks has extensive attention notable success. Based on our longstanding efforts interests chemistry, we review herein research advances participated medium. magnified image

Язык: Английский

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Recent advances in visible light-mediated chemical transformations of enaminones

Chinese Chemical Letters, Год журнала: 2023, Номер 35(2), С. 108977 - 108977

Опубликована: Авг. 26, 2023

Язык: Английский

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The Domino Chromone Annulation and a Transient Halogenation-Mediated C–H Alkenylation toward 3-Vinyl Chromones

Organic Letters, Год журнала: 2020, Номер 22(24), С. 9518 - 9523

Опубликована: Дек. 3, 2020

Reported in this paper is a step economical method toward the general synthesis of 3-vinyl chromones via reactions between readily available o-hydroxyphenyl enaminones and various alkenes. The domino C–H alkenylation chromone annulation are involved, which enables products using both terminal internal alkenes key process transient halogenation.

Язык: Английский

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Transition metal-free synthesis of 3-trifluoromethyl chromones via tandem C–H trifluoromethylation and chromone annulation of enaminones

Organic Chemistry Frontiers, Год журнала: 2020, Номер 7(18), С. 2770 - 2775

Опубликована: Янв. 1, 2020

The synthesis of 3-trifluoromethyl chromones has been realized via transition metal-free reactions o-hydroxyphenyl enaminones and the Langlois reagent cascade C–H trifluoromethylation chromone annulation.

Язык: Английский

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Recent Advances in Organic Synthesis Based on N,N-Dimethyl Enaminones

Synthesis, Год журнала: 2020, Номер 53(04), С. 587 - 610

Опубликована: Ноя. 3, 2020

Abstract Enaminones are gaining increasing interest because of their unique properties and importance in organic synthesis as versatile building blocks. N,N-Dimethyl enaminones offer a better leaving group (a dimethylamine group) than other enaminones, allow further elaboration via range facile chemical transformations. Over the past five years, there have been an number reports describing synthetic applications N,N-dimethyl enaminones. This review provides comprehensive overview on that reported since 2016. 1 Introduction 2 Direct C(sp2)–H α-Functionalization 2.1 Synthesis α-Sulfenylated 2.2 α-Thiocyanated 2.3 α-Acyloxylated 3 Functionalization Reactions C=C Double Bond Cleavage 3.1 Functionalized Methyl Ketones 3.2 α-Ketoamides, α-Ketoesters 1,2-Diketones 3.3 N-Sulfonyl Amidines 4 Construction All-Carbon Aromatic Scaffolds 4.1 Benzaldehydes 4.2 Naphthalenes 5 Heterocyclic 5.1 Five-Membered Heterocycles 5.2 Six-Membered 5.3 Quinolines 5.4 Chromones 5.5 Other Fused Polycyclic 6 Conclusions Perspectives

Язык: Английский

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Copper-catalyzed C–H/N–H annulation of enaminones and alkynyl esters for densely substituted pyrrole synthesis

Chemical Communications, Год журнала: 2022, Номер 58(11), С. 1808 - 1811

Опубликована: Янв. 1, 2022

Herein, the copper-catalyzed annulation of enaminones with alkynyl esters for facile synthesis different pyrroles a 2,3,4,5-tetrasubstituted structure has been developed. With Cu(OAc)2 as only catalyst, tunable 2-vinyl and 2,3-dicarboxyl-functionalized achieved by using terminal internal esters, respectively. The represents first example accessing substituted via direct cascade reactions involving vinylation pyrrole ring formation.

Язык: Английский

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Recent advances in transition metal-catalyzed transformations in N,N-disubstituted enaminones

Tetrahedron Letters, Год журнала: 2023, Номер 130, С. 154766 - 154766

Опубликована: Сен. 26, 2023

Язык: Английский

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Transition metal-free tunable synthesis of 3-(trifluoromethylthio) and 3-trifluoromethylsulfinyl chromones via domino C-H functionalization and chromone annulation of enaminones

Chinese Chemical Letters, Год журнала: 2024, Номер 35(11), С. 109683 - 109683

Опубликована: Март 2, 2024

Язык: Английский

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Iodine-Promoted Thioylation and Dicarbonylation of Enaminone α-C Sites: Synthesis of Fully Substituted Thiazoles via C═C Bond Cleavage

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(4), С. 2505 - 2515

Опубликована: Фев. 5, 2024

A novel iodine-promoted difunctionalization of α-C sites in enaminones was demonstrated as a means synthesizing variety fully substituted thiazoles by constructing C–C(CO), C–S, and C–N bonds. This transformation allows the realization unusual aryl C2 synthons simultaneously thioylation dicarbonylation sites. preliminary mechanistic study performed indicated that cleavage C═C bonds involves bicyclization/ring-opening oxidative coupling sequence.

Язык: Английский

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