Recent Developments in Disulfide Bond Formation

Witt, Dariusz

doi:10.1055/s-2008-1067188

Cited by 228 publications

(146 citation statements)

References 35 publications

(39 reference statements)

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“…The activation of such chemical reaction occurs in the presence of oxygen [47] and plays a critical role in biochemistry because it prevents the folding of some proteins and their oxidation [37]. The reaction of two terminal -SH groups of neighbouring rows causes the formation of disulfide −S-S− covalent bonds.…”

Section: Resultsmentioning

confidence: 99%

Alkylthiol self-assembled monolayers on Au(111) with tailored tail groups for attaching gold nanoparticles

et al. 2017

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To cite this version:V Y Kutsenko, L Lopatina, Léo Bossard-Giannesini, O Marchenko, Olivier Pluchery, et al.. Alkylthiol self-assembled monolayers on Au(111) with tailored tail groups for attaching gold nanoparticles. Nanotechnology, Institute of Physics, 2017, 28 (23) by their tail groups: 1,9-nonanedithiol (NDT) and 1,4-butanedithiol (BDT) and 11-mercaptoundecanol (MUOH). STM reveals very different morphologies: hexagonal lattice for MUOH and parallel rows for NDT and BDT. In the case of NDT, we find that the thiol tail groups may form disulfide bridges for long immersion times. The availability of -SH group for chemical reactions is checked by attaching gold nanoparticles (AuNPs). When the thiol tail group is available, AuNPs readily attach as shown with atomic force microscopy (AFM). When disulfide bridges are formed the gold surface is not able to bind nanoparticles.

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Section: Resultsmentioning

confidence: 99%

Alkylthiol self-assembled monolayers on Au(111) with tailored tail groups for attaching gold nanoparticles

et al. 2017

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“…[1][2][3][4][5][6][7][8] Owing to the increasing importance of the disulfides (disulfanes) in chemistry [9][10][11][12][13][14] and biology, [15][16][17] synthetic approaches for their preparation have been extensively studied. [18][19][20][21][22] According to the literature, disulfides can be obtained directly from *Corresponding author. Email: khalili@shirazu.ac.ir thiocyanates, [23][24][25] alcohols [26][27][28] and sulfonyl chlorides.…”

Section: Introductionmentioning

confidence: 99%

4,4′-Azopyridine as an easily prepared and recyclable oxidant for synthesis of symmetrical disulfides from thiols or alkyl halides(tosylates)/thiourea

Khalili

Iranpoor

Firouzabadi

2015

Journal of Sulfur Chemistry

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Heterocyclic azo compounds, prepared from corresponding amines in one step, are used as effective oxidants for the conversion of thiols into symmetrical disulfides in high yields. Among the studied azo compounds, 4,4 -azopyridine was found to be very efficient for the odorless conversion of alkyl halides into disulfides in the presence of thiourea. An attractive feature of this azo compound is that its obtained solid side product hydrazine is easily separated by filtration and can be recycled to its azo compound for further use.

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“…1). 6 In a remarkable S N Ar, sulfur-linked porphyrin dimers were generated via a simple deprotection of a thioether appended porphyrin. While our initial goal was the synthesis of a free thiol group directly attached to the porphyrin macrocycle via base deprotection, bisporphyrin products were observed predominantly.…”

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confidence: 99%

From thioether substituted porphyrins to sulfur linked porphyrin dimers: an unusual S_NAr via thiolate displacement?

et al. 2014

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a Treatment of meso 2-ethylhexyl-3-mercaptopropionate substituted porphyrins with base at room temperature generated a porphyrin thiolate anion which in situ reacted in a nucleophilic aromatic substitution (S N Ar) reaction with remaining thioether derivative. This reaction yielded S-linked bisporphyrins in good yields, with mechanistic insight obtained via displacement reactions. Additionally, S N Ar of the thioether chain was achieved using S-and organolithium nucleophiles.Owing to their biological and medical importance, 1 the synthesis of organosulfur compounds has been the focus of thorough investigations. 2 One important development is the nucleophilic aromatic substitution (S N Ar) with the thiolate anion. 3 Typically, thiolate S N Ar only occurs with activated aryls with leaving groups such as halides or tosylates, 4 requiring a very strong base, elevated temperature and/or the use of metal catalysts. 3c,5 Additionally, it is often hindered via competing oxidation reactions to form disulfide bonds ( Fig. 1). 6 In a remarkable S N Ar, sulfur-linked porphyrin dimers were generated via a simple deprotection of a thioether appended porphyrin. While our initial goal was the synthesis of a free thiol group directly attached to the porphyrin macrocycle via base deprotection, bisporphyrin products were observed predominantly. Such sulfur linked bisporphyrins have not previously been reported and are easily produced, in contrast to other heteroatom linked porphyrin arrays which generally require many synthetic steps. 7These were generated via S N Ar by the thiolate at the meso position of the substituted porphyrin, with isooctyl-3-mercaptopropionate acting as an excellent leaving group. Substitution reactions on porphyrins are limited, 8 at best, and typically require highly specific activated systems and high temperatures. However, this room temperature in situ S N Ar of a seemingly unactivated porphyrin in such fashion represents, to the best of our knowledge, the first reaction of this type to be documented. This is somewhat reminiscent of previous work in our group, whereby using organolithium reagents a variety of substituents can be introduced to the porphyrin periphery via S N type reactions. 9Porphyrins bearing thiol and thioether substituents have a diverse range of optical applications due to their ability to form self-assembled monolayers (SAMs) on gold surfaces 10 and this attribute formed the basis for our interest in thioporphyrins. Adopting a versatile Pd-catalyzed porphyrin-sulfur bond forming reaction developed by Itoh and Mase, 11 a library of novel isooctyl-3-mercaptopropionate substituted porphyrins, so-called protected thiols, were synthesized. 12This involved a Pd-catalyzed reaction of bromoporphyrins 1a-i and the thiol 2-ethylhexyl-3-mercaptopropionate in good to excellent yields of 66-87%. These protected thiols have the potential to be used in Au-NP formulation or as a photosensitizer delivery system in PDT, 13 but our primary goal was for their use in deprotection reactions (Table 1). A...

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Recent Developments in Disulfide Bond Formation

Cited by 228 publications

References 35 publications

Alkylthiol self-assembled monolayers on Au(111) with tailored tail groups for attaching gold nanoparticles

Alkylthiol self-assembled monolayers on Au(111) with tailored tail groups for attaching gold nanoparticles

4,4′-Azopyridine as an easily prepared and recyclable oxidant for synthesis of symmetrical disulfides from thiols or alkyl halides(tosylates)/thiourea

From thioether substituted porphyrins to sulfur linked porphyrin dimers: an unusual S_NAr via thiolate displacement?

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Recent Developments in Disulfide Bond Formation

Cited by 228 publications

References 35 publications

Alkylthiol self-assembled monolayers on Au(111) with tailored tail groups for attaching gold nanoparticles

Alkylthiol self-assembled monolayers on Au(111) with tailored tail groups for attaching gold nanoparticles

4,4′-Azopyridine as an easily prepared and recyclable oxidant for synthesis of symmetrical disulfides from thiols or alkyl halides(tosylates)/thiourea

From thioether substituted porphyrins to sulfur linked porphyrin dimers: an unusual SNAr via thiolate displacement?

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From thioether substituted porphyrins to sulfur linked porphyrin dimers: an unusual S_NAr via thiolate displacement?