Expeditious synthesis of 1-substituted taurines with diverse functionalized side-chains

Kakaei, Saeed; Chen, Ning; Xu, Jiaxi

doi:10.1016/j.tet.2012.10.029

Cited by 29 publications

(9 citation statements)

References 24 publications

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“…BzXan used in this study was synthesized as previously reported (Supporting Information, Figs. S1–S3) . To investigate the formation of BzSH via xanthate deprotection a model study was conducted by treating BzXan with 1.2 equivalents of n‐ butyl amine in toluene.…”

Section: Figurementioning

confidence: 99%

“…S1-S3). 31 To investigate the formation of BzSH via xanthate deprotection a model study was conducted by treating BzXan with 1.2 equivalents of n-butyl amine in toluene. The product, BzSH, was isolated in high yield and characterized by 1 H and 13 C nuclear magnetic resonance (NMR) spectroscopy and chemical ionization mass spectroscopy (Supporting Information, Figs.…”

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confidence: 99%

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In situ xanthate deprotection to generate thiol chain transfer agents for conventional free radical linear and branched vinyl polymerization

Flynn

Dale

Dwyer

et al. 2017

J. Polym. Sci. Part A: Polym. Chem.

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Branched polymers have received considerable interest over recent decades due to their unique properties including complex architectures, low viscosities, good solubility, and high numbers of potentially diverse terminal functional groups. [1][2][3] The preparation of branched polymers by conventional free radical polymerization (FRP) of mixtures of mono-vinyl and multi-vinyl monomers is somewhat limited due to the onset of gelation following excessive crosslinking, which may readily occur at low monomer conversion. 4 Nonetheless, a number of branched polymer architectures have been reported using various strategies including the chain transfer monomer approach, 5-8 homopolymerization of multi-functional monomers; 9-12 gelation is prevented in the latter case through excessive dilution, employing solvents exhibiting high transfer constants or by utilizing excessive amounts of initiator at high temperature. Another approach, commonly referred to as the Strathclyde methodology, involves the copolymerization of mono-and bi-functional monomers in the presence of a chain transfer agent (CTA). [13][14][15] The resulting branched polymers contain a large number of conjoined primary chains that are chemically near-identical to linear polymers generated in the absence of the bi-functional monomer; consequently, the statistical nature of the branching generates broad molecular weight distributions and a range of species with varying numbers of chain-ends. The Strathclyde methodology has received significant attention in the literature with the majority of publications relying on the use of thiol-based CTAs. [16][17][18][19][20] Whilst thiols have been extensively studied as CTAs in the FRP of a wide range of monomers, they have considerable malodor, may exhibit acute toxicity and readily undergo oxidation under atmospheric conditions, 21 which generates handling problems during industrial scale processing. 22 The synthesis of thiolbased CTAs containing bespoke structures remains a difficult task and as a result the range of CTA structures studied is generally heavily dependent on commercial availability thiols, thereby limiting the diversity of research scope. Routes that allow ready synthesis of a diverse range of thiols, or synthetic equivalents of thiols, for use in FRP would offer access to new chain end functionality via readily scale-able syntheses.Dithiocarbonates (xanthates) offer an efficient protecting group chemistry for thiols, they can be synthesized without difficulty and readily undergo deprotection in the presence of primary amines under ambient conditions. 23 We have recently reported the use of xanthates as thiol protecting groups for the synthesis and surface group modification of low generation thiol-functional dendrimers, linear-dendritic hybrids, and hyper-branched polydendrons, using a one-pot deprotection/ functionalization strategy. [24][25][26] Thiocarbonyl containing compounds, including xanthates, dithiobenzoates, dithiocarbamates and trithiocarbonates, are commonly used to provide control with...

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Section: Figurementioning

confidence: 99%

mentioning

confidence: 99%

In situ xanthate deprotection to generate thiol chain transfer agents for conventional free radical linear and branched vinyl polymerization

Flynn

Dale

Dwyer

et al. 2017

J. Polym. Sci. Part A: Polym. Chem.

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“…Preparation of the xanthates 1 a , [20] 1 b , [21] 1 c , [22] 1 d , [13] 1 f , [23] 1 k , [24] 1 n , [25] 1 p , [26] 1 q , [27] 1 r [27] asd 1 s , [23] have already been described in the literature.…”

Section: Methodsmentioning

confidence: 99%

“…Methyl 2‐((ethoxycarbonothioyl)thio)acetate (1 r) [27] . Light yellowish oil (3.46 g, 89 %); 1 H NMR (700 MHz, DMSO‐d 6 ) δ=4.61 (q, J =7.1 Hz, 2H), 4.06 (s, 2H), 3.67 (s, 3H), 1.34 (t, J =7.1 Hz, 3H); 13 C NMR (75 MHz, DMSO‐d 6 ) δ=212.6, 168.1, 70.7, 52.4, 36.9, 13.4; HRMS (ESI): m/z calcd for C 6 H 11 O 3 S 2 + : 195.0144 [M+H] + ; found: 195.0149.…”

Section: Methodsmentioning

confidence: 99%

Xanthates as Thiol Surrogates for Nucleophilic Substitution with Aryl Halides

et al. 2021

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We herein report an unprecedented xanthate‐based protocol for the preparation of aryl‐alkyl thioethers. Heating xanthates with aryl halides and namely cesium carbonate in methanol provides the target thioethers in generally good yields within short reaction times. This method allows one to avoid contact with odorous thiols and also to introduce substituents of which the corresponding thiols are virtually unavailable or inconvenient in use.

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“…Addition of either stoichiometric methyl chloroacetate/CuCl, or methyl bromoacetate/CuBr to 5a in xylene at 135 °C in analogy to, failed with only ca . 1% conversion after 8 h. The radical addition of methyl [(ethoxycarbonothioyl)sulfanyl]acetate to 5a was not more successful and we did not attempted these conditions on the protected corresponding acetal . The more expensive Mukayama ‐type conjugated addition was also not considered …”

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confidence: 99%

A One Pot Synthesis of Dehydrohedione (DHH) from a Hedione^® Precursor

Chapuis

Richard

2018

Helvetica Chimica Acta

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Dehydrohedione (DHH) 1a was obtained via a one pot, three step, domino procedure in 54% overall yield from 2a, by treatment with CuBr2, in MeOH at 65 °C. We demonstrated that the direct transformation of malonate derivative 2a into DHH 1a under CuX2 Kochi's conditions goes preferentially through the pathway involving intermediates 2b/2c and 7a, rather than 3a/3b or 8a/8b, essentially via α‐halogenation/dehydrohalogenation of the ketone moiety, both mediated by CuX2, while in‐situ decarbomethoxylation is promoted by the resulting CuX in refluxing MeOH.

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Expeditious synthesis of 1-substituted taurines with diverse functionalized side-chains

Cited by 29 publications

References 24 publications

In situ xanthate deprotection to generate thiol chain transfer agents for conventional free radical linear and branched vinyl polymerization

In situ xanthate deprotection to generate thiol chain transfer agents for conventional free radical linear and branched vinyl polymerization

Xanthates as Thiol Surrogates for Nucleophilic Substitution with Aryl Halides

A One Pot Synthesis of Dehydrohedione (DHH) from a Hedione^® Precursor

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Expeditious synthesis of 1-substituted taurines with diverse functionalized side-chains

Cited by 29 publications

References 24 publications

In situ xanthate deprotection to generate thiol chain transfer agents for conventional free radical linear and branched vinyl polymerization

In situ xanthate deprotection to generate thiol chain transfer agents for conventional free radical linear and branched vinyl polymerization

Xanthates as Thiol Surrogates for Nucleophilic Substitution with Aryl Halides

A One Pot Synthesis of Dehydrohedione (DHH) from a Hedione® Precursor

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A One Pot Synthesis of Dehydrohedione (DHH) from a Hedione^® Precursor