Enantioselective intermolecular [2 + 2] photocycloadditions of vinylazaarenes with triplet-state electron-deficient olefins

Tian, Dong; Sun, Xin; Cao, Shanshan; Wang, Er-Meng; Yin, Yanli; Zhao, Xiaowei

doi:10.1016/s1872-2067(22)64156-1

Cited by 12 publications

(2 citation statements)

References 52 publications

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“…Moreover, the triplet energy of 3 and 1 a were measured to be 62.0 and 65.5 kcal/mol, respectively (see Supporting Information for details). Thus, Ir‐1 (E T =61.8 kcal/mol) [13l] and Ir‐2 (E T =62.0 kcal/mol) [17] are able to promote 3 to its triplet state while DPZ (E T =46.4 kcal/mol) [13t] is unable to undergo energy transfer with 3 , in agreement with the high yields of 4 observed with Ir‐1 and Ir‐2 and the exclusive formation of hydroarylation product 3 when DPZ was used as the photocatalyst (Schemes 2 and 3). Taken together, DPZ can only promote the photooxidation of 4‐hydroxycoumarins while Ir‐2 is capable of achieving both the photooxidation and the subsequent [2+2] cycloaddition.…”

Section: Resultsmentioning

confidence: 99%

Divergent Photosensitizer Controlled Reactions of 4‐Hydroxycoumarins and Unactivated Olefins: Hydroarylation and Subsequent [2+2] Cycloaddition

Chang,

Pang,

2023

Angew Chem Int Ed

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Herein, we report a photoinduced approach for hydroarylation of unactivated olefins using 4‐hydroxycoumarins as the arylating reagent. Key to the success of this reaction is the conversion of nucleophilic 4‐hydroxycoumarins into electrophilic carbon radicals via photocatalytic arene oxidation, which not only circumvents the polarity‐mismatch issue encountered under ionic conditions but also accommodates a broad substrate scope and inhibits side reactions that were previously observed. Moreover, divergent reactivity was achieved by changing the photocatalyst, enabling a subsequent [2+2] cycloaddition to deliver cyclobutane‐fused pentacyclic products that are otherwise challenging to access in high yields and with high diastereoselectivity. Mechanistic studies have elucidated the mechanism of the reactions and the origin of the divergent reactivity.

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Section: Resultsmentioning

confidence: 99%

Divergent Photosensitizer Controlled Reactions of 4‐Hydroxycoumarins and Unactivated Olefins: Hydroarylation and Subsequent [2+2] Cycloaddition

Chang,

Pang,

2023

Angew Chem Int Ed

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“…In recent years, our group has devoted considerable effort to visible light-driven photochemical synthesis, [11][12][13][14][15][16] where bsubstituted enones were used in the catalytic asymmetric reductive azaarylation. 15 In addition to experiencing singleelectron reduction, these olens are prone to E/Z isomerization and homocoupling, triggered by the formation of triplet species via energy transfer or direct excitation.…”

Section: Introductionmentioning

confidence: 99%

Visible light-driven dearomative ring expansion of (aza)arenes to access dihydrofuran-based polycyclic compounds

Zhang,

You,

Ban

et al. 2024

Chem. Sci.

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Synergistic Dual Photoredox and Chiral Hydrogen Bonding Catalysis: Recent Advances

Selvakumar

2023

Asian J Org Chem

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In the last two decades, chiral hydrogen bonding catalysis has been enormously utilized to trigger several valuable synthetic transformations. Similarly, modern day radical chemistry has witnessed the potency of visible light photoredox catalysis to generate radicals via single electron transfer pathway. Recently, their cooperative effect has proved to be a key strategy to access many elegant transformations that are only feasible under the synergistic action of these two catalytic systems. This dual catalytic system demonstrates high efficiency for introducing molecular complexity in an enantioselective fashion. In this mini review, we have compiled the most recent development of this dual catalytic system that surfaced in the last three years with particular attention paid to the mechanistic details and its substrate scope. We hope that this mini review will provide readers with a brief overview of the advancement and application of photoredox catalysts and chiral hydrogen bond donors for synergistic dual catalytic reactions.

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Enantioselective intermolecular [2 + 2] photocycloadditions of vinylazaarenes with triplet-state electron-deficient olefins

Cited by 12 publications

References 52 publications

Divergent Photosensitizer Controlled Reactions of 4‐Hydroxycoumarins and Unactivated Olefins: Hydroarylation and Subsequent [2+2] Cycloaddition

Divergent Photosensitizer Controlled Reactions of 4‐Hydroxycoumarins and Unactivated Olefins: Hydroarylation and Subsequent [2+2] Cycloaddition

Visible light-driven dearomative ring expansion of (aza)arenes to access dihydrofuran-based polycyclic compounds

Synergistic Dual Photoredox and Chiral Hydrogen Bonding Catalysis: Recent Advances

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