Phototrifluoromethylsulfenylation of phenylcyclopropane

Munavalli, S.; Rossman, D. I.; Rohrbaugh, D. K.; Durst, H. D.

doi:10.1016/s0022-1139(98)00136-5

Cited by 17 publications

(3 citation statements)

References 44 publications

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“…Of note, the photocatalyzed ring fission of phenylcyclopropane was evaluated in the presence of trifluoromethanesulfenyl chloride, but this reaction resulted in a mixture of products 17…”

Section: The Historical Background Of Trifluoromethylthiolationmentioning

confidence: 99%

Direct Trifluoromethylthiolation Reactions: The “Renaissance” of an Old Concept

2014

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Because of its high lipophilicity, the CF3S group has always interested chemists. However, strategies to introduce it into organic molecules have been, for the most part, reserved to specialized “fluorine chemists”. Recent published work has demystified these preconceived ideas by proposing new efficient methods or easy‐to‐handle reagents to enrich the toolbox of chemists. However, all these new concepts arise from the pioneering works of the past! In this review, we will do a “back to the future” by remembering the most significant results of the past and by presenting extensions and novelties of the present and for the future.

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“…Of note, the photocatalyzed ring fission of phenylcyclopropane was evaluated in the presence of trifluoromethanesulfenyl chloride, but this reaction resulted in a mixture of products 17…”

Section: The Historical Background Of Trifluoromethylthiolationmentioning

confidence: 99%

Direct Trifluoromethylthiolation Reactions: The “Renaissance” of an Old Concept

2014

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“…Among them, the radical trifluoromethylthiolation represents one of the most attractive approach for incorporation of SCF 3 into organic molecules . Traditionally, the SCF 3 radicals can be generated from trifluoromethanethiol(CF 3 SH), trifluoromethanesulyenyl chloride (CF 3 SCl) and bistrifluoromethyl disulfide (CF 3 SSCF 3 ), but highly toxic and hard‐to‐handle reagents are required. More modern approache is employing the in situ oxidation of AgSCF 3 as the source of SCF 3 radical .…”

Section: Methodsmentioning

confidence: 99%

Synthesis of SCF₃‐Containing Benzoxazines and Oxazolines via a Photoredox‐Catalyzed Radical Trifluoromethylthiolation‐Cyclization of Olefinic Amides

Zhu

You

et al. 2019

Asian J Org Chem

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“…However, only mass spectrometric characterization was provided for the products. 19a Likewise, the photocatalyzed reaction of 1-cyclopropyl-1-phenylprop-2-yn-1-ol ( 47 ) with ClSCF 3 in acetonitrile with the aid of a 100-W mercury lamp furnished a complex mixture of products containing seven compounds (Scheme 9 ). In addition to replacement of the hydroxyl group, addition across the C≡C bond as well as cleavage of the cyclopropyl ring were observed.…”

Section: Photocatalyzed Trifluoromethylthiolationmentioning

confidence: 99%

Progress in Photocatalyzed Trifluoromethylthiolation and Trifluoromethylselenolation Reactions

Li,

Song,

Zhang

et al. 2024

Synthesis

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Photoredox catalysis has evolved into a widely used method and has fostered the extensive utilization of radical coupling partners in organic synthesis over the past years. The integration of visible-light photocatalysis into fluorine chemistry has achieved many important transformations for radical fluorination and fluoroalkylation, which usually proceeded smoothly under mild conditions with simple oxidants or reductants, exhibiting a broad range of substrates and excellent functional group tolerance. In this review, we highlight the photoredox-catalyzed procedures for the trifluoromethylthiolation and trifluoromethylselenolation reactions as well as their possible mechanisms. The ease and environment-friendliness of shuttling electrons back and forth to substrates or intermediates, and selectively transferring energy through visible-light-absorbing catalysts or EDA complexes holds promise to improve the trifluoromethylthiolation and trifluoromethylselenolation in radical chemistry.

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Phototrifluoromethylsulfenylation of phenylcyclopropane

Cited by 17 publications

References 44 publications

Direct Trifluoromethylthiolation Reactions: The “Renaissance” of an Old Concept

Direct Trifluoromethylthiolation Reactions: The “Renaissance” of an Old Concept

Synthesis of SCF₃‐Containing Benzoxazines and Oxazolines via a Photoredox‐Catalyzed Radical Trifluoromethylthiolation‐Cyclization of Olefinic Amides

Progress in Photocatalyzed Trifluoromethylthiolation and Trifluoromethylselenolation Reactions

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Phototrifluoromethylsulfenylation of phenylcyclopropane

Cited by 17 publications

References 44 publications

Direct Trifluoromethylthiolation Reactions: The “Renaissance” of an Old Concept

Direct Trifluoromethylthiolation Reactions: The “Renaissance” of an Old Concept

Synthesis of SCF3‐Containing Benzoxazines and Oxazolines via a Photoredox‐Catalyzed Radical Trifluoromethylthiolation‐Cyclization of Olefinic Amides

Progress in Photocatalyzed Trifluoromethylthiolation and Trifluoromethylselenolation Reactions

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Synthesis of SCF₃‐Containing Benzoxazines and Oxazolines via a Photoredox‐Catalyzed Radical Trifluoromethylthiolation‐Cyclization of Olefinic Amides