Recent advances in transition metal-catalyzed heteroannulative difunctionalization of alkenes via C–H activation for the synthesis of heterocycles

Organic Chemistry Frontiers, Год журнала: 2022, Номер 9(8), С. 2256 - 2279

Опубликована: Янв. 1, 2022

In this review article, we summarized recent advances in the transition metal-catalyzed heteroannulative difunctionalization of alkenes via direct C–H activation to access heterocyclic frameworks.

Язык: Английский

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Palladium/TY-Phos-Catalyzed Asymmetric Heck/Tsuji–Trost Reaction of o-Bromophenols with 1,3-Dienes

Journal of the American Chemical Society, Год журнала: 2023, Номер 145(8), С. 4378 - 4383

Опубликована: Фев. 16, 2023

2,3-Dihydrobenzofurans are crucial building blocks in the synthesis of natural products and pharmaceutical molecules. However, their asymmetric has been a long-standing formidable challenge so far. In this work, we developed highly enantioselective Pd/TY-Phos-catalyzed Heck/Tsuji-Trost reaction o-bromophenols with various 1,3-dienes, allowing expedient access to chiral substituted 2,3-dihydrobenzofurans. This features excellent regio- enantiocontrol, high functional group tolerance, easy scalability. More importantly, demonstration method as valuable tool for construction optically pure (R)-tremetone fomannoxin is highlighted.

Язык: Английский

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Coupling partner-dependent unsymmetrical C–H functionalization of N-phenoxyacetamides leading to sophisticated spirocyclic scaffolds

Organic Chemistry Frontiers, Год журнала: 2022, Номер 9(17), С. 4583 - 4590

Опубликована: Янв. 1, 2022

In this paper, a coupling partner-dependent unsymmetrical C–H functionalization of N -phenoxyacetamides leading to the formation sophisticated spirocyclic scaffolds is presented.

Язык: Английский

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Asymmetric cascades of the π-allyl complex: a journey from transition-metal catalysis to metallaphotocatalysis

Chemical Communications, Год журнала: 2023, Номер 59(76), С. 11298 - 11319

Опубликована: Янв. 1, 2023

The enantioselective catalytic cascade involving Tsuji-Trost allylation has provided a viable strategy for the construction of multiple asymmetric C-C and C-X centres numerous methods have been developed around it synthesis various vital scaffolds. synthetic utility this was enhanced by replacing customary allyl acetates with ethylene diacetates/dicarbonates, vinyl epoxides, oxetanes, carbonates, cyclopropanes, enynes, dienes using transition-metal catalysis. One more milestone achieved when metallaphotocatalysis necessary platform these cascades cheaper metal. This review will provide summary from 2015.

Язык: Английский

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Base-tuned selective 1,2-dichloromethylhydroxylation and 1,2-peroxyhydroxylation of 1,3-dienes via a tandem radical process

Chemical Communications, Год журнала: 2023, Номер 59(62), С. 9481 - 9484

Опубликована: Янв. 1, 2023

A catalyst-free 1,2-difunctionalization of 1,3-dienes with CHCl3 and TBHP in the presence NEt3 to give dichloromethylhydroxylation products was developed. Various substituents on aryl ring dienes tolerated reactions gave corresponding moderate good yields. When Na2CO3 employed as base, key intermediate α-amino radical could not be formed; therefore, 1,2-peroxyhydroxylation were obtained instead. This protocol provides an effective functional group tolerant strategy for diene 1,2-difunctionalization, thus providing great potential further functionalization modification synthetic molecules.

Язык: Английский

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Half-Sandwich d6-Metal (CoIII, RhIII, IrIII, RuII)-Catalyzed Enantioselective C–H Activation

SynOpen, Год журнала: 2023, Номер 07(04), С. 466 - 485

Опубликована: Сен. 6, 2023

Abstract Transition-metal-catalyzed enantioselective C–H activation provides a straightforward strategy to synthesize chiral molecules from readily available sources. In this graphical review, we summarize the progress on half-sandwich d6-metal (CoIII, RhIII, IrIII, RuII)-catalyzed functionalization reactions. The review is categorized according type of metal catalyst and ligand employed. Representative enantio-determining models catalytic cycles are presented.

Язык: Английский

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Copper(I)-Catalyzed Dearomatization of Benzofurans with 2-(Chloromethyl)anilines through Radical Addition and Cyclization Cascade

Organic Letters, Год журнала: 2024, Номер 26(2), С. 519 - 524

Опубликована: Янв. 8, 2024

Herein, we described a copper(I)-catalyzed dearomatization of benzofurans with 2-(chloromethyl)anilines to prepare various tetrahydrobenzofuro[3,2-

Язык: Английский

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Cobalt(III)-Catalyzed Regio- and Chemoselective [4 + 2]-Annulation of N-Chlorobenzamides/Acrylamides with 1,3-Dienes at Room Temperature

The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(9), С. 5713 - 5729

Опубликована: Апрель 12, 2022

Co(III)-catalyzed regio- and chemoselective redox-neutral C-H annulation of arylamides/acrylamides with 1,3-dienes is described. The present reaction was well suited a less-reactive 1,3-butadiene. By employing this protocol, pharmaceutically important 3,4-dihydroisoquinolinones were synthesized in good yields. Furthermore, the prepared converted into highly oxirane derivatives A plausible mechanistic cycle proposed supported by competition experiment kinetic isotopic effect (KIE) studies.

Язык: Английский

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Rhodium-catalyzed enantioselective annulation of N-phenoxyacetamides with 1,3-dienes

Science China Chemistry, Год журнала: 2023, Номер 66(10), С. 2842 - 2846

Опубликована: Июнь 6, 2023

Язык: Английский

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Cobalt-Catalyzed Z to E Geometrical Isomerization of 1,3-Dienes

The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(7), С. 4712 - 4723

Опубликована: Март 11, 2022

An efficient cobalt-catalyzed geometrical isomerization of 1,3-dienes is described. In the combination a CoCl2 precatalyst with an amido-diphosphine-oxazoline ligand, E/Z mixtures proceed in stereoconvergent manner, affording (E) isomers high stereoselectivity. This facile transformation features broad substrate scope good functional group tolerance and could be scaled up to gram scale smoothly catalyst loading 1 mol %.

Язык: Английский

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