Rh(III)-Catalyzed Dienylation and Cyclopropylation of 1,2,3-Benzotriazinones with Alkylidenecyclopropanes

Organic Letters, Год журнала: 2023, Номер 25(28), С. 5179 - 5184

Опубликована: Июль 6, 2023

Rh (III)-catalyzed dienylation and cyclopropylation of 1,2,3-benzotriazinones with alkylidenecyclopropanes (ACPs) has been achieved. Different from the previous reports 1,2,3-benzotriazinones, triazinone ring remained intact in this C-H bond functionlization reaction. Also, denitrogenative could also be realized by changing reaction temperature. This protocol is featured high E selectivity, wide substrate scope, divergent structures products.

Язык: Английский

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Regioselective Synthesis of 3‐Substituted Isocoumarin‐1‐imines via Palladium‐Catalyzed Denitrogenative Transannulation of 1,2,3‐Benzotriazin‐4(3H)‐ones and Terminal Alkynes

Chemistry - An Asian Journal, Год журнала: 2023, Номер 18(21)

Опубликована: Сен. 15, 2023

A palladium-catalyzed denitrogenative transannulation strategy to access various 3-substituted isocoumarin-1-imine frameworks using 1,2,3-benzotriazin-4(3H)-ones and terminal alkynes is described. The reaction highly regioselective tolerates a wide range of functional groups. believed proceed via five-membered palladacycle intermediate extruding environmentally benign molecular nitrogen as by-product. utility this method was showcased through the one-pot synthesis biologically relevant isocoumarin scaffolds.

Язык: Английский

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Enantioselective domino alkyl arylation of vinyl phosphonates by combining photoredox and nickel catalysis

Green Synthesis and Catalysis, Год журнала: 2024, Номер unknown

Опубликована: Апрель 1, 2024

A nickel/photoredox mediated asymmetric domino alkyl arylation of vinyl phosphonates to generate a diverse array enantioenriched α-aryl is disclosed. This three-component difunctionalization couples aryl halides and bromides with phosphonates, exhibiting excellent chemo- regioselectivity under mild reaction conditions. The method avoids the need for pre-formed organometallics phosphorus halides. Mechanistic DFT studies suggest that photoexcited [4CzIPN]* oxidizes diethyl 1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate (HEH) [4CzIPN]•–, which then reduces bromide form radicals undergo Giese addition phosphonate. At same time, Ni0 oxidatively adds followed by enantiodetermining oxidative radical trapping phosphonate-based tetrahedral NiII center reductive elimination. Independent gradient model based on Hirshfeld partition (IGMH) analysis suggests orientation phosphonate group (P=O…π interaction) expected play an essential role in controlling enantioselectivity.

Язык: Английский

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Ru(II)-Catalyzed C–H Amination of 1,2,3-Benzotriazinones with Azide Compounds

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(17), С. 12249 - 12254

Опубликована: Авг. 8, 2024

A Ru(II)-catalyzed directed C–H amination of 1,2,3-benzotriazinones with azide compounds has been reported. The reaction a wide substrate scope organic azides good results and represents useful pathway to the construction versatile heterocyclic amino products. In addition, method can be used for phthalazinones, highlighting synthetic practicability strategy.

Язык: Английский

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A sequential olefin hydroboration/Suzuki coupling for denitrogenative alkylation of benzotriazinones with α-olefins

Journal of Organometallic Chemistry, Год журнала: 2024, Номер 1022, С. 123383 - 123383

Опубликована: Сен. 21, 2024

Язык: Английский

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Electrochemical annulation of 1,2,3-benzotriazinones with alkynes to access isoquinolin-1(2H)-ones

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(36), С. 7295 - 7299

Опубликована: Янв. 1, 2023

An eco-friendly approach for electrochemical radical cascade annulation of 1,2,3-benzotriazinones with alkynes is described. Under catalyst-free and external reductant-free electrolysis conditions, a range isoquinolin-1(2H)-ones were obtained in moderate to good yields. Cyclic voltammetry control studies suggest that the reaction proceeds via pathway. Furthermore, this could be easily scaled up.

Язык: Английский

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Nickel/photoredox-catalyzed enantioselective arylation of α-chloro thioesters

Chemical Communications, Год журнала: 2023, Номер 59(89), С. 13355 - 13358

Опубликована: Янв. 1, 2023

The first dual nickel/photoredox-catalyzed enantioselective reductive cross-coupling of racemic α-chloro thioesters with aryl iodides has been developed. This strategy avoids the need for organometallic reagents or stoichiometric metal reductants. reaction could tolerate a wide range substrate scope excellent reactivity and high enantioselectivities (up to 91% ee) access variety chiral α-aryl thioesters. synthetic utility corresponding is demonstrated. Furthermore, we explored mechanism such an radical process.

Язык: Английский

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Rh(III)‐Catalyzed Selective C−H Alkylation and Alkenylation of 1,2,3‐Benzotriazinones with Maleimides

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(17), С. 3646 - 3652

Опубликована: Июнь 25, 2024

Abstract Herein, we describe a reaction conditions‐based switchable Rh(III)‐catalyzed C−H alkylation and alkenylation of 1,2,3‐benzotriazinones with maleimides, where the triazinone serves as directing group rather than its traditional role denitrogenative precursor. This strategy enables selective synthesis diverse 3‐arylated succinimides maleimides in up to 99% yield broad substrate scope (48 examples). Furthermore, for first time, tandem coupling has been achieved by slightly modifying conditions. Additionally, gram‐scale reactions product derivatizations were conducted demonstrate synthetic utility.

Язык: Английский

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Metal-Catalyzed Divergent Synthesis from Ylides with 3-arylbenzo[d][1,2,3]triazin-4(3H)-ones

Chemical Communications, Год журнала: 2024, Номер 60(88), С. 12928 - 12931

Опубликована: Янв. 1, 2024

The present work reveals a new metal-catalyzed synthetic reaction involving 1,2,3-benzotriazinones with carbonyl sulfoxonium ylide and iodonium ylide, resulting in divergent products.

Язык: Английский

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Photoredox Catalyzed Tandem Denitrogenative [4 + 2] Annulation of 1,2,3-Benzotriazin-4(3H)-ones with Terminal Olefins

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(21), С. 16043 - 16048

Опубликована: Окт. 15, 2024

The dihydroisoquinolones skeleton is ubiquitous in natural products and biological molecules. Reported strategies for constructing usually require noble metal catalysts or stoichiometric oxidants, which limit their wide applications. Herein, we developed a photoredox catalyzed tandem denitrogenative [4 + 2] annulation reaction of 1,2,3-benzotriazin-4(3H)-ones with terminal olefins. A variety can be accessed moderate to excellent yield. This protocol features high atom-economy, mild conditions, external oxidant-free, enabling the synthesis various substituted dihydroisoquinolones.

Язык: Английский

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