Synthesis of Redshifted Azobenzene Photoswitches by Late-Stage Functionalization

Azobenzenes are versatile photoswitches that can be cycled between their trans‐ and cis‐configuration with light. The wavelengths required for this isomerization are substantially shifted from the UV to the visible range through tetra‐ortho‐chlorination. These halogenated azobenzenes display unique...

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Published inChemistry : a European journal Vol. 22; no. 13; pp. 4364 - 4368
Main Authors Konrad, David B., Frank, James A., Trauner, Dirk
Format Journal Article
LanguageEnglish
Published WEINHEIM Blackwell Publishing Ltd 18.03.2016
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Abstract Azobenzenes are versatile photoswitches that can be cycled between their trans‐ and cis‐configuration with light. The wavelengths required for this isomerization are substantially shifted from the UV to the visible range through tetra‐ortho‐chlorination. These halogenated azobenzenes display unique photoswitching characteristics, but their syntheses remain limited and inefficient. A new general method for the synthesis of tetra‐ortho‐chloro azobenzenes has been developed, which relies on direct palladium(II)‐catalyzed C−H activation of pre‐existing standard azobenzenes. This late‐stage functionalization has a broad substrate scope and can be used to create a variety of useful building blocks for the construction of more elaborate redshifted photopharmaceuticals. This method is used to prepare red‐AzCA‐4, a photoswitchable vanilloid that enables optical control of the cation channel TRPV1 with visible light. A redshift in photopharmacology: Palladium(II) acetate effectively catalyzes the selective tetra‐ortho‐chlorination of azobenzenes. This methodology provides a straightforward and general approach towards the synthesis of these otherwise challenging redshifted photoswitches. This procedure is used to synthesize red‐AzCA‐4 (see scheme; NCS=N‐chlorosuccinimide), which is a potent photochromic agonist for the vanilloid receptor 1.
AbstractList Azobenzenes are versatile photoswitches that can be cycled between their trans- and cis-configuration with light. The wavelengths required for this isomerization are substantially shifted from the UV to the visible range through tetra-ortho-chlorination. These halogenated azobenzenes display unique photoswitching characteristics, but their syntheses remain limited and inefficient. A new general method for the synthesis of tetra-ortho-chloro azobenzenes has been developed, which relies on direct palladium(II)-catalyzed C-H activation of pre-existing standard azobenzenes. This late-stage functionalization has a broad substrate scope and can be used to create a variety of useful building blocks for the construction of more elaborate redshifted photopharmaceuticals. This method is used to prepare red-AzCA-4, a photoswitchable vanilloid that enables optical control of the cation channel TRPV1 with visible light.
Azobenzenes are versatile photoswitches that can be cycled between their trans ‐ and cis ‐configuration with light. The wavelengths required for this isomerization are substantially shifted from the UV to the visible range through tetra‐ ortho ‐chlorination. These halogenated azobenzenes display unique photoswitching characteristics, but their syntheses remain limited and inefficient. A new general method for the synthesis of tetra‐ ortho ‐chloro azobenzenes has been developed, which relies on direct palladium(II)‐catalyzed C−H activation of pre‐existing standard azobenzenes. This late‐stage functionalization has a broad substrate scope and can be used to create a variety of useful building blocks for the construction of more elaborate redshifted photopharmaceuticals. This method is used to prepare red ‐ AzCA‐4 , a photoswitchable vanilloid that enables optical control of the cation channel TRPV1 with visible light.
Azobenzenes are versatile photoswitches that can be cycled between their trans‐ and cis‐configuration with light. The wavelengths required for this isomerization are substantially shifted from the UV to the visible range through tetra‐ortho‐chlorination. These halogenated azobenzenes display unique photoswitching characteristics, but their syntheses remain limited and inefficient. A new general method for the synthesis of tetra‐ortho‐chloro azobenzenes has been developed, which relies on direct palladium(II)‐catalyzed C−H activation of pre‐existing standard azobenzenes. This late‐stage functionalization has a broad substrate scope and can be used to create a variety of useful building blocks for the construction of more elaborate redshifted photopharmaceuticals. This method is used to prepare red‐AzCA‐4, a photoswitchable vanilloid that enables optical control of the cation channel TRPV1 with visible light. A redshift in photopharmacology: Palladium(II) acetate effectively catalyzes the selective tetra‐ortho‐chlorination of azobenzenes. This methodology provides a straightforward and general approach towards the synthesis of these otherwise challenging redshifted photoswitches. This procedure is used to synthesize red‐AzCA‐4 (see scheme; NCS=N‐chlorosuccinimide), which is a potent photochromic agonist for the vanilloid receptor 1.
Azobenzenes are versatile photoswitches that can be cycled between their trans- and cis-configuration with light. The wavelengths required for this isomerization are substantially shifted from the UV to the visible range through tetra-ortho-chlorination. These halogenated azobenzenes display unique photoswitching characteristics, but their syntheses remain limited and inefficient. A new general method for the synthesis of tetra-ortho-chloro azobenzenes has been developed, which relies on direct palladium(II)-catalyzed C-H activation of pre-existing standard azobenzenes. This late-stage functionalization has a broad substrate scope and can be used to create a variety of useful building blocks for the construction of more elaborate redshifted photopharmaceuticals. This method is used to prepare red-AzCA-4, a photoswitchable vanilloid that enables optical control of the cation channel TRPV1 with visible light. A redshift in photopharmacology: Palladium(II) acetate effectively catalyzes the selective tetra-ortho-chlorination of azobenzenes. This methodology provides a straightforward and general approach towards the synthesis of these otherwise challenging redshifted photoswitches. This procedure is used to synthesize red-AzCA-4 (see scheme; NCS=N-chlorosuccinimide), which is a potent photochromic agonist for the vanilloid receptor1.
Author Trauner, Dirk
Konrad, David B.
Frank, James A.
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BackLink https://www.ncbi.nlm.nih.gov/pubmed/26889884$$D View this record in MEDLINE/PubMed
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Issue 13
Keywords azobenzene
RECEPTOR
COORDINATION
halogenation
ion channels
AZO-COMPOUNDS
OPTICAL CONTROL
ORTHO-HALOGENATION
C-H activation
CATALYTIC METHOD
CHANNEL
GLUTAMATE
IN-VIVO
FLUOROAZOBENZENES
photopharmacology
C−H activation
Language English
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Snippet Azobenzenes are versatile photoswitches that can be cycled between their trans‐ and cis‐configuration with light. The wavelengths required for this...
Azobenzenes are versatile photoswitches that can be cycled between their trans- and cis-configuration with light. The wavelengths required for this...
Azobenzenes are versatile photoswitches that can be cycled between their trans ‐ and cis ‐configuration with light. The wavelengths required for this...
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SubjectTerms Activation
Azo Compounds - chemical synthesis
Azo Compounds - chemistry
azobenzene
Capsaicin receptors
Catalysis
Cations
Channels
Chemistry
Chemistry, Multidisciplinary
Chlorination
Construction
C−H activation
Halogenation
Hydrogen Bonding
ion channels
Isomerism
Isomerization
Light
Light effects
Optical control
Palladium
Photochemical Processes
photopharmacology
Physical Sciences
Red shift
Science & Technology
Synthesis
TRPV Cation Channels - chemistry
Wavelengths
Title Synthesis of Redshifted Azobenzene Photoswitches by Late-Stage Functionalization
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