Photocatalyst and additive-free visible light induced trifluoromethylation–arylation of<i>N</i>-arylacrylamides with Umemoto's reagent

Ma, Pengju; Yang, Bo; Zhao, Xu; Huang, Xuan; Zhang, Junmin

doi:10.1039/d0cc07502g

Cited by 31 publications

(14 citation statements)

References 68 publications

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“…The reaction is proposed to proceed through an ortho ‐quinone methide before a terminal malonitrile‐mediated [4+2] cyclization step to form the trifluoromethylated product. Huang, Zhang, and coworkers showed the synthesis of trifluoromethylated 2‐oxindoles utilizing 23 under metal‐free blue light irradiation [159] …”

Section: Trifluoromethylation (Cf3)mentioning

confidence: 99%

Recent Advances in Visible Light‐Mediated Radical Fluoro‐alkylation, ‐alkoxylation, ‐alkylthiolation, ‐alkylselenolation, and ‐alkylamination

Lin

Coe

Krishnamurti

et al. 2023

The Chemical Record

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In the last few years, many reagents and protocols have been developed to allow for the efficient fluorofunctionalization of a diverse set of scaffolds ranging from alkanes, alkenes, alkynes, and (hetero)arenes. The concomitant rise of organofluorine chemistry and visible light‐mediated synthesis have synergistically expanded the fields and have mutually benefitted from developments in both fields. In this context, visible light driven formations of radicals containing fluorine have been a major focus for the discovery of new bioactive compounds. This review details the recent advances and progress made in visible light‐mediated fluoroalkylation and heteroatom centered radical generation.

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Section: Trifluoromethylation (Cf3)mentioning

confidence: 99%

Recent Advances in Visible Light‐Mediated Radical Fluoro‐alkylation, ‐alkoxylation, ‐alkylthiolation, ‐alkylselenolation, and ‐alkylamination

Lin

Coe

Krishnamurti

et al. 2023

The Chemical Record

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“…[61] An analogous method was also reported, which utilized cheap TfCl. [62] In 2018, Cai and coworkers reported that irradiation of CF 3 SO 2 Na with blue LEDs in the presence of an organic photocatalyst and some oxygen (which served as final electron acceptor) is also efficient for this transformation. [63] Finally, Huang, Zhang, and coworkers have recently reported a very mild and simple photochemical method, which did not require any photocatalyst or additive (Scheme 18).…”

Section: Scheme 11 Photochemical Trifluoromethylative Transformation ...mentioning

confidence: 99%

Recent Progress in Aryltrifluoromethylation Reactions of Carbon‐Carbon Multiple Bonds

Remete

Nonn

Novák

et al. 2022

Chemistry An Asian Journal

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Due to the increasing relevance of fluorinecontaining organic molecules in drug design, the synthesis of organofluorine compounds has gained high significance in synthetic organic chemistry. Trifluoromethylative difunctionalizations of carbon-carbon multiple bonds, with the simultaneous incorporation of a CF 3 group and another functional element, have considerable potential. Because of the high importance of carbon-carbon bond-forming reactions in organic synthesis, carbotrifluoromethylations and, in particular, aryltrifluoromethylations or heteroaryltrifluoromethylations are considered to be increasing fields of synthetic organic chemistry. The aim of the current review is to summarize recent developments of aryltrifluoromethylation or heteroaryltrifluoromethylation reactions.

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“…CF 3 radical precursor under mild reaction conditions (Scheme 30). [50] The strategy neither required a photocatalyst nor a base and afforded the target products in moderate to good yields. The N ‐arylacrylamides with electron‐withdrawing and electron‐donating groups performed efficiently, delivering the target products in excellent yields.…”

Section: Cyclization Approachmentioning

confidence: 99%

Visible Light Mediated Synthesis of Oxindoles

Singh

Sharma

2021

Adv Synth Catal

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Functionalized oxindoles are privileged heterocyclic scaffolds and common core structural motifs that are broadly present in numerous natural products and serve as key intermediates in the synthesis of biological products, agrochemicals, and pharmaceuticals. Oxindoles exhibit a broad pharmacological and physiological activities, and diverse range of applications in medicinal chemistry and biomedical research. Owing to these fascinating biological and physiological activities of oxindoles, several methodologies have been developed for the construction of oxindoles. In the past decade, the visible light mediated methodologies have attracted substantial attention and emerged as a promising approach for the construction of oxindoles. In this review, the visible light mediated synthesis of oxindoles have been described.

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Photocatalyst and additive-free visible light induced trifluoromethylation–arylation ofN-arylacrylamides with Umemoto's reagent

Abstract: A visible light induced highly convenient and practical method for the trifluoromethyl–arylation of N-arylmethacrylamides has been developed using Umemoto*s reagent as the trifluoromethyl source.

Cited by 31 publications

References 68 publications

Recent Advances in Visible Light‐Mediated Radical Fluoro‐alkylation, ‐alkoxylation, ‐alkylthiolation, ‐alkylselenolation, and ‐alkylamination

Recent Advances in Visible Light‐Mediated Radical Fluoro‐alkylation, ‐alkoxylation, ‐alkylthiolation, ‐alkylselenolation, and ‐alkylamination

Recent Progress in Aryltrifluoromethylation Reactions of Carbon‐Carbon Multiple Bonds

Visible Light Mediated Synthesis of Oxindoles

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