Visible-Light-Mediated NHC and Tertiary Amine Catalysis Enabling α-H Acylation of Alkenes

Li, Shihao; Wang, Sheng; Feng, Huiyi; Tang, Fei; Yang, Wenqing; Li, Xiaoxuan; Zhang, Qi; Fan, Shilu; Feng, Yi‐Si

doi:10.1021/acs.orglett.3c00802

Cited by 6 publications

(4 citation statements)

References 38 publications

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“…In 2023, the groups of Zhang, Fan, and Feng reported another strategy for regioselective CÀ H acylation of styrene derivatives with aroyl fluorides by applying the triple-catalytic system consisting of an NHC catalyst, an iridium photocatalyst and quinuclidine (Scheme 26). [45] This cooperative catalysis allows for the coupling of styrenyl substrates with aroyl fluorides for the synthesis of α,β-unsaturated ketones with good functional group tolerance. In contrast to the Studer's report, not SET, but energy transfer between 38 and the Ir-photocatalyst is proposed to occur to form excited acyl azolium cation 39.…”

Section: Merging Nhc/photoredox Catalysis With Tertiary Amine Catalys...mentioning

confidence: 99%

Catalytic Synthesis of Carbonyl Compounds Using Acyl Fluorides, Carbamoyl Fluorides, and Fluoroformates: An Overview

Jung,

Lee,

Shin

2024

Asian J Org Chem

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Acyl fluorides, carbamoyl fluorides and fluoroformates have been employed as efficient reagents in a number of organic syntheses. Their application in catalytic transformations, however, began to be explored in the early 2000s. Recently, these reagents have increasingly gained attention owing to their unique reactivity in diverse catalytic systems. This review aims to overview the advancements in the development of catalytic processes, including transition‐metal catalysis, organocatalysis, and cooperative NHC/photoredox catalysis, where these organofluorine compounds are employed as acyl, carbamoyl, and ester group donors.

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Section: Merging Nhc/photoredox Catalysis With Tertiary Amine Catalys...mentioning

confidence: 99%

Catalytic Synthesis of Carbonyl Compounds Using Acyl Fluorides, Carbamoyl Fluorides, and Fluoroformates: An Overview

Jung,

Lee,

Shin

2024

Asian J Org Chem

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“…Feng, Fan, Zhang, and their co-workers reported a similar α-acylation of alkenes 35 of which a tertiary amine 220 catalyst was used to instead of the sulfinate (Scheme ). Key steps involve the single electron oxidation of tertiary amine 220 to aminol radical cation 221 , which subsequently adds to alkene 35 to generate carbon radical 222 . Radical-cross coupling of the resulting carbon radical 222 with the NHC-bound ketyl radical 26 followed by releasing the NHC catalyst and the tertiary amine eventually afford the target α-acylated alkenes.…”

Section: Miscellaneous Photoredox Cooperative Catalysis Of Acylazoliu...mentioning

confidence: 99%

Radical Reactions with N-Heterocyclic Carbene (NHC)-Derived Acyl Azoliums for Access to Multifunctionalized Ketones

Cai,

Yang,

Ren

et al. 2024

ACS Catal.

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As one of the most important key intermediates, NHC-bound acylazolium-based ionic transformations have been intensively explored in the past two decades. With the expeditious development of NHC-catalyzed radical transformations in recent years, NHC-bound acylazolium chemistry has reached another level, with the number of relevant publications increasing significantly. However, a summary focused on radical acylations of NHC-derived acyl azoliums classified according to the mechanistic difference has not been reported. Such a detailed classification and deep analysis provide opportunities for a better understanding of the history and trend of this field. In this review, radical reactions with N-heterocyclic carbene (NHC)-derived acyl azoliums are systematically introduced. The achievements and challenges within this area are also summarized and discussed at the end.

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“…Very recently, Feng and co-workers further developed an intermolecular direct α-CÀ H acylation of alkenes by the visiblelight-mediated NHC/ tertiary amine catalysis, affording a range of α-substituted vinyl ketones (Scheme 38). [54]…”

Section: α-Acylation Of Alkenesmentioning

confidence: 99%

Radical Acylation of Alkenes by NHC‐Organocatalysis

Tang,

Du,

Gao

2023

Eur J Org Chem

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N‐Heterocyclic carbene (NHC) catalyzed radical‐radical reactions have been proven to be powerful strategies for assembling ketyl‐containing compounds via single electron transfer (SET) pathway under either thermal conditions or photoredox conditions. In this context, acylation of alkenes via radical relay under NHC‐organocatalysis has also opened a new window for the difunctionalization of alkenes to construct valuable molecules in organic synthesis. In this review, the advances and progress of the acylation of alkenes via NHC‐organocatalysis were summarized according to different ways of generation of the key NHC‐bound ketyl‐type radicals. Furthermore, reaction scopes, limitations and mechanisms were discussed based on reaction types and catalytic systems. Conclusions and perspectives were also put forward at the end.

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Visible-Light-Mediated NHC and Tertiary Amine Catalysis Enabling α-H Acylation of Alkenes

Cited by 6 publications

References 38 publications

Catalytic Synthesis of Carbonyl Compounds Using Acyl Fluorides, Carbamoyl Fluorides, and Fluoroformates: An Overview

Catalytic Synthesis of Carbonyl Compounds Using Acyl Fluorides, Carbamoyl Fluorides, and Fluoroformates: An Overview

Radical Reactions with N-Heterocyclic Carbene (NHC)-Derived Acyl Azoliums for Access to Multifunctionalized Ketones

Radical Acylation of Alkenes by NHC‐Organocatalysis

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