Continuous Visible‐Light Photoflow Approach for a Manganese‐Catalyzed (Het)Arene C−H Arylation

Liang, Yu‐Feng; Steinbock, Ralf; Yang, Long; Ackermann, Lutz

doi:10.1002/ange.201805644

Cited by 30 publications

(12 citation statements)

References 156 publications

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“…[9] While this strategy employing unconventional TM photocatalysts has notably led to attractive reactivities in coupling reactions, [10] the field of visible light induced TM catalyzed C À Hfunctionalization still requires catalyst engineering to address the various challenges associated with the selective transformation of unactivated CÀHb onds. [11] Organoboron compounds are versatile intermediates for medicinal chemistry and materials science and the direct CÀH borylation of arenes is arguably the most straightforward approach to access these useful building blocks. [12] Despite the recent advances made in TM catalyzed site-selective C À H borylation, [13] only poor regioselectivities have been observed with the few reported photocatalytic systems that rely on the use of less attractive high-energy UV light ( Figure 1c).…”

Section: Thedirectfunctionalizationofinertcàhbondshasemergedmentioning

confidence: 99%

Visible Light Induced Rhodium(I)‐Catalyzed C−H Borylation

et al. 2019

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An efficient visible light induced rhodium(I)catalyzedr egioselective borylation of aromatic C À Hb onds is reported. The photocatalytic system is based on asingle NHC À Rh I complex capable of both harvesting visible light and enabling the bond breaking/forming at room temperature.The chelating nature of the NHC-carboxylate ligand was critical to ensure the stability of the Rh I complex and to provide excellent photocatalytic activities.E xperimental mechanistic studies evidenced ap hotooxidative ortho C À Hb ond addition upon irradiation with blue LEDs,leading to acyclometalated Rh IIIhydride intermediate.

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Section: Thedirectfunctionalizationofinertcàhbondshasemergedmentioning

confidence: 99%

Visible Light Induced Rhodium(I)‐Catalyzed C−H Borylation

et al. 2019

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“…F o r ptrifluoromethylbenzenedizonium tetrafluoroborate and benzene, by switching to flow, an improvement in yield from 25% to 64% was noted with a productivity of 1.42 g h −1 . The methodology was also applied to the synthesis of a precursor of the hyperthermia drug Dantrolene, starting from furfural derived from biomass [197].…”

Section: − H Alkenylationmentioning

confidence: 99%

Pushing the boundaries of C–H bond functionalization chemistry using flow technology

2020

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C-H functionalization chemistry is one of the most vibrant research areas within synthetic organic chemistry. While most researchers focus on the development of small-scale batch-type transformations, more recently such transformations have been carried out in flow reactors to explore new chemical space, to boost reactivity or to enable scalability of this important reaction class. Herein, an up-to-date overview of C-H bond functionalization reactions carried out in continuous-flow microreactors is presented. A comprehensive overview of reactions which establish the formal conversion of a C-H bond into carbon-carbon or carbonheteroatom bonds is provided; this includes metal-assisted C-H bond cleavages, hydrogen atom transfer reactions and C-H bond functionalizations which involve an S E-type process to aromatic or olefinic systems. Particular focus is devoted to showcase the advantages of flow processing to enhance C-H bond functionalization chemistry. Consequently, it is our hope that this review will serve as a guide to inspire researchers to push the boundaries of C-H functionalization chemistry using flow technology.

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“…In 2018, Ackermann and co-workers reported manganese catalyzed C–H arylation in flow setup merging with blue LED (Fig. 9A, ii ) 115 . Superior yields as compared with batch processes and use of earth-abundant transition metal as catalyst were some major merits of the established protocol.…”

Section: Introductionmentioning

confidence: 99%

Traditional and sustainable approaches for the construction of C–C bonds by harnessing C–H arylation

et al. 2022

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Biaryl scaffolds are found in natural products and drug molecules and exhibit a wide range of biological activities. In past decade, the transition metal-catalyzed C–H arylation reaction came out as an effective tool for the construction of biaryl motifs. However, traditional transition metal-catalyzed C–H arylation reactions have limitations like harsh reaction conditions, narrow substrate scope, use of additives etc. and therefore encouraged synthetic chemists to look for alternate greener approaches. This review aims to draw a general overview on C–H bond arylation reactions for the formation of C–C bonds with the aid of different methodologies, majorly highlighting on greener and sustainable approaches.

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Continuous Visible‐Light Photoflow Approach for a Manganese‐Catalyzed (Het)Arene C−H Arylation

Cited by 30 publications

References 156 publications

Visible Light Induced Rhodium(I)‐Catalyzed C−H Borylation

Visible Light Induced Rhodium(I)‐Catalyzed C−H Borylation

Pushing the boundaries of C–H bond functionalization chemistry using flow technology

Traditional and sustainable approaches for the construction of C–C bonds by harnessing C–H arylation

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