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“Click-Triazole” Coordination Chemistry: Exploiting 1,4-Disubstituted-1,2,3-Triazoles as Ligands

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Click Triazoles

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 28))

Abstract

Access to readily functionalized ligand architectures is of crucial importance in a range of different areas including catalysis, metallopharmaceuticals, bioimaging, metallosupramolecular chemistry, mechanically interlocked architectures, and molecular machines. The mild and modular Cu(I)-catalyzed 1,3-cycloaddition of terminal alkynes with organic azides (the CuAAC “click” reaction) allows the ready formation of functionalized 1,4-disubstituted-1,2,3-triazole scaffolds, and this has led to an explosion of interest in the coordination chemistry of these heterocycles. The parent 1,4-disubstituted-1,2,3-triazole units can potentially act as monodentate or bridging ligands. Examples of both the monodentate (through either the N3 nitrogen or C5 carbon positions of the 1,2,3-triazole) and bridging (through the N2 and N3 nitrogen atoms) coordination modes have been structurally characterized. A diverse array of bi-, tri-, and polydentate ligands incorporating 1,4-disubstituted-1,2,3-triazole units have also been synthesized and characterized. When the chelate pocket involves coordination through the N3 nitrogen atom of the 1,2,3-triazole, these are called “regular” click ligands. While these are the most common type of “click” chelate, “inverse” ligands in which the 1,2,3-triazole unit coordinates through the less electron-rich N2 nitrogen atom have also been synthesized and characterized. The resulting “click” complexes are beginning to find applications in catalysis, metallosupramolecular chemistry, photophysics, and as metallopharmaceuticals and bioimaging agents.

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Notes

  1. 1.

    A referee has suggested to us that L'abbé was the first to report the CuAAC reaction in the literature, see [8].

  2. 2.

    While the mild Ag2O method is most commonly used for the generation of these 1,3,4-trisubstituted-1,2,3-triazol-5-ylidene complexes, an alternative approach in which the free carbene is generated by deprotonation of the precusor triazolium salt with KOtBu then complexed to a metal salt also leads to the formation of the desired carbene complexes, see [137, 139].

Abbreviations

[9]aneS3:

1,4,7-Trithiacyclonoane

AAC:

Azide-alkyne cycloaddition

Ac:

Acetyl

Acac:

Acetylacetonate

Ad:

Adamantyl

Ar:

Aryl

ATH:

Asymmetric transfer hydrogenation

ATRP:

Atom transfer radical polymerization

Bn:

Benzyl

Boc:

Tert-butoxycarbonyl

Bpy:

2,2′-Bipyridyl

Bu:

Butyl

Bz:

Benzoyl

CAN:

Ceric ammonium nitrate

cod:

Cyclooctadiene

Cp*:

1,2,3,4,5-Pentamethylcyclopentadiene

CuAAC:

Cu(I)-catalyzed azide-alkyne cycloaddition

d:

Day(s)

DABCO:

1,4-Diazabicyclo[2.2.2]octane

DFT:

Density functional theory

Dipp:

3,5-Diisopropylphenyl

Dmbpy:

4,4′-Dimethyl-2,2′-bipyridyl

DME:

1,2-Dimethoxyethane

DMEDA:

N N, ′-dimethyl-1,2-ethylenediamine

DMF:

Dimethylformamide

DMSO:

Dimethyl sulfoxide

Dppb:

Bis(diphenylphosphino)butane

DSSC:

Dye-sensitized solar cells

ECL:

Electrochemiluminescence

EDTA:

Ethylenediaminetetraacetic acid

ee:

Enantiomer excess

Equiv:

Equivalent(s)

ESI-MS:

Electrospray ionization mass spectrometry

Et:

Ethyl

F2ppy:

2-(2,4-Difluoro)phenylpyridine

Fc:

Ferrocene

h:

Hour(s)

i-Pr:

Isopropyl

LEECs:

Light-emitting electrochemical cell

MAO:

Methylaluminoxane

Me:

Methyl

MeCN:

Acetonitrile

Mes:

Mesityl (2,4,6-trimethylphenyl)

min:

Minute(s)

Nap:

Naphthalene

NHC:

N-heterocyclic carbene

OLEDs:

Organic light-emitting diodes

Ph:

Phenyl

Pic:

Picolinic acid

ppy:

Phenylpyridine

Pr:

Propyl

PS:

Polystyrene

py:

Pyridine

RAFT:

Reversible addition-fragmentation chain transfer

RT:

Room temperature

RuAAC:

Ru(II)-catalyzed azide-alkyne cycloaddition

Salen:

N N, ′-ethylenebis(salicylimine)

SCO:

Spin crossover

SEC:

Size-exclusion chromatography

t-Bu:

Tert-butyl

TEP:

Tolman electronic parameter

Tf:

Trifluoromethanesulfonyl (triflyl)

THF:

Tetrahydrofuran

TMEDA:

N,N,N′,N′-tetramethyl-1,2-ethylenediamine

TMS:

Trimethylsilyl

TOF:

Turnover frequency

Tol:

4-Methylphenyl

TON:

Turnover number

Ts:

Tosyl (4-toluenesulfonyl)

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  1. Department of Chemistry, University of Otago, 56, Dunedin, New Zealand

    James D. Crowley & David A. McMorran

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    Janez Košmrlj

Addendum

Addendum

This review initially covered the field up to June 30, 2011, and while the manuscript was under review, the area has continued to grow with additional examples of bi- [230–232], tri- [233–237], and polydentate [238, 239] “click” ligands appearing in literature.

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Crowley, J.D., McMorran, D.A. (2012). “Click-Triazole” Coordination Chemistry: Exploiting 1,4-Disubstituted-1,2,3-Triazoles as Ligands. In: Košmrlj, J. (eds) Click Triazoles. Topics in Heterocyclic Chemistry, vol 28. Springer, Berlin, Heidelberg. https://doi.org/10.1007/7081_2011_67

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