Photocatalytic Synthesis of Allylic Trifluoromethyl Substituted Styrene Derivatives in Batch and Flow

Kreis, Lukas M.; Krautwald, Simon; Pfeiffer, Nicole; Martin, Rainer E.; Carreira, Erick M.

doi:10.1021/ol400410m

Cited by 126 publications

(62 citation statements)

References 47 publications

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“…9 Their report focuses on the photochemical synthesis of important allylic trifluoromethanes ( 13 ) from iodomethyltrifluoromethane and styrenes. Although highly innovative, this method required high catalyst loading to drive the reaction to completion.…”

Section: Visible Light-induced Co-catalyzed Reactionsmentioning

confidence: 99%

Visible light-induced transition metal-catalyzed transformations: beyond conventional photosensitizers

2017

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Employment of simple transition metal (TM= Co, Fe, Cu, Pd, Pt, Au)-based photocatalyst (PC) led to the dramatic acceleration of known TM-catalyzed reactions, as well as to the discovery of unprecedented chemical transformations. Compared to the conventional cooperative/dual photocatalysis (type B, Figure 1), this new class of unconventional PCs operates via a single photoexcitation/catalytic cycle, where the TM complex plays a “double duty” role by harvesting light and catalyzing the chemical transformation. Also, these TM photocatalysts participate in the bond-forming/breaking event in the transformation via a substrate-TM interaction, an aspect that is uncommon for conventional photocatalysis (type A, Figure 1). This tutorial review highlights the recent advances in this emerging area.

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Section: Visible Light-induced Co-catalyzed Reactionsmentioning

confidence: 99%

Visible light-induced transition metal-catalyzed transformations: beyond conventional photosensitizers

2017

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“…This alternative bond construction strategy that complements existing approaches provides trifluoroethylated styrene derivatives in moderate to good yields and as a single 68 min (flow protocol), however, the conversion did not exceed the 65 % which is similar to that obtained in batch protocol. 114 4.-SUMMARY 6. [100] Remarkably, in contrast to most photocatalytic processes MacMillan_s system does not require any sacrificial oxidant or reductant by its design; both oxidation and reduction steps are productive and lead to the formation of the desired product.…”

Section: Miscellaneousmentioning

confidence: 99%

Photocatalytic fluoroalkylation reactions of organic compounds

2015

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“…1b)2829303132. Unfortunately, while many C–H trifluoroethylation methods have been reported333435363738, there are fewer reagents for the trifluoroethylation of amines (Fig. 1a, left)3940.…”

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confidence: 99%

A practical and catalyst-free trifluoroethylation reaction of amines using trifluoroacetic acid

2017

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Amines are a fundamentally important class of biologically active compounds and the ability to manipulate their physicochemical properties through the introduction of fluorine is of paramount importance in medicinal chemistry. Current synthesis methods for the construction of fluorinated amines rely on air and moisture sensitive reagents that require special handling or harsh reductants that limit functionality. Here we report practical, catalyst-free, reductive trifluoroethylation reactions of free amines exhibiting remarkable functional group tolerance. The reactions proceed in conventional glassware without rigorous exclusion of either moisture or oxygen, and use trifluoroacetic acid as a stable and inexpensive fluorine source. The new methods provide access to a wide range of medicinally relevant functionalized tertiary β-fluoroalkylamine cores, either through direct trifluoroethylation of secondary amines or via a three-component coupling of primary amines, aldehydes and trifluoroacetic acid. A reduction of in situ-generated silyl ester species is proposed to account for the reductive selectivity observed.

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Photocatalytic Synthesis of Allylic Trifluoromethyl Substituted Styrene Derivatives in Batch and Flow

Cited by 126 publications

References 47 publications

Visible light-induced transition metal-catalyzed transformations: beyond conventional photosensitizers

Visible light-induced transition metal-catalyzed transformations: beyond conventional photosensitizers

Photocatalytic fluoroalkylation reactions of organic compounds

A practical and catalyst-free trifluoroethylation reaction of amines using trifluoroacetic acid

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