Synthesis of novel dithiocarbamates and xanthates using dialkyl azodicarboxylates: S N bond formation

Halimehjani, Azim Ziyaei; Klepetářová, Blanka; Beier, Petr

doi:10.1016/j.tet.2018.02.049

Cited by 13 publications

(10 citation statements)

References 77 publications

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“…These O,S ‐diesters react with secondary amines to generate N,N ‐disubstituted dithiocarbamates (Scheme , previous work 4) . A one−pot three−component reaction of amines, CS 2 and a dialkyl azodicarboxylates was reported to generate N,N ‐disubstituted dithiocarbamates . These two methods for disubstituted dithiocarbamates are particularly suitable for aliphatic amines.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of N,N‐Disubstituted Thiocarbamates from Thiocarbamoyl Fluorides with Alcohols/Phenols/Thiophenols/Thioalcohols Through Copper Catalysis

2019

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Traditional methods for preparing N,N‐disubstituted thiocarbamates require highly toxic, flammable and volatile reagents, or their derivatives. Recently, we developed a general method for thiocarbamoyl fluorides from safe, cheap, and easily available starting materials. Reported reactions involving thioyl fluoride with nucleophiles are very scarce. In this report, copper catalyzed reaction of thiocarbamoyl fluorides with phenols/thiophenols/alcohols/thioalcohols under Na2CO3 at 50 °C or at 80 °C in CH3CN were first developed, affording the corresponding N,N‐disubstituted thiocarbamates in moderate to excellent yields. When alcohols are cheap and their boiling points are less than 120 °C or they are water‐soluble, CuCl catalyzed reaction of thiocarbamoyl fluorides with alcohols at 50 °C was also developed. The reaction has good functional group tolerance. Methoxy, methyl, chloro, bromo, nitro, even ester functional groups were all tolerated. Control reactions demonstrated that copper catalyst played the key role on the success of these novel reactions.

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Section: Methodsmentioning

confidence: 99%

Synthesis of N,N‐Disubstituted Thiocarbamates from Thiocarbamoyl Fluorides with Alcohols/Phenols/Thiophenols/Thioalcohols Through Copper Catalysis

2019

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“…Beier and research group invented a novel one‐pot three‐component pathway to synthesize a new class of dithiocarbamates or xanthates without using any catalyst (Scheme 39). [49] The dithiocarbamic acid were prepared in situ by reaction between amine and CS 2 and further addition on to dialkylazodicarboxylates in acetic acid at −40 °C gave the desired products with a new S−N bond. Aliphatic primary and secondaty amine reacted well under optimized conditions.…”

Section: S−n Bond Forming Reactionsmentioning

confidence: 99%

Progress of Dialkyl Azodicarboxylates in Organic Transformations

Singh

Mritunjay

2021

Asian J Org Chem

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In recent past, dialkyl azodicarboxylates have been embraced as versatile reagents in synthetic strategies other than Mitsunobu reactions. These azo compounds have been utilized as an oxidant or dehydrogenating reagent in oxidative transformations, such as cross dehydrogenative coupling, oxidative Ugi-type reaction, dehydrogenation etc. Moreover, they have been utilized in different types of bond construction like C-Heteroatom (C-Het) and SÀ N bond. Very recently, these azo compounds have also been explored in photochemical reactions. Such types of reported reactions and their reaction pathways are presented here in this minireview, which manifested the oxidative abilities and advantageous features of dialkyl azodicarboxylates.

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“…All rights reserved. 6,2.8 Hz,1H),2.82 (dd,J = 16.3,9.5 Hz,1H),2.66 (dd,J = 16.3,3.8 Hz,1H) ppm; 13 C NMR (101 MHz,CDCl3) δ 197.6,170.2,134.2,133.7,129.3,129.2,62.9,52.3,49.8,34.9,33.4 2.34 (s, 3H) ppm; 13 C NMR (101 MHz,CDCl3) δ 197.1,170.3,138.1,132.1,129.7,127.9,62.8,52.3,50.3,34.6,33.3,21.2…”

Section: Accepted Manuscriptmentioning

confidence: 99%

“…During the past decade, we have shown that in situ prepared dithiocarbamic acids obtained from amines and carbon disulfide are efficient nucleophiles in reactions with diverse electrophiles, including electron-deficient and electron-rich alkenes, 1 alkynes, 2 epoxides, 3 nitroepoxides, 4 aldehydes, 5 dialkyl azodicarboxylates, 6 Togni reagent, 7 sultones, 8 and others. 9 In situ prepared dithiocarbamic acid can react with electrophiles as a mono-or bis-nucleophile, with the sulfur or the nitrogen atom.…”

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confidence: 99%

Tandem Alkylation/Michael Addition Reaction of Dithiocarbamic Acids with Alkyl γ-Bromocrotonates: Access to Functionalized 1,3-Thiazolidine-2-thiones

et al. 2021

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Thiazolidine-2-thiones were prepared via a novel multicomponent reaction of primary amines (amino acids), carbon disulfide and γ-bromocrotonates. The reaction proceeds via a domino alkylation/intramolecular Michael addition to provide the corresponding thiazolidine-2-thiones in high to excellent yields. Using diamines in this protocol, bis(thiazolidine-2-thiones) derivatives were synthesized. The synthetic utility of adducts was demonstrated by hydrolysis, amidation and oxidation reactions.

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Synthesis of novel dithiocarbamates and xanthates using dialkyl azodicarboxylates: S N bond formation

Cited by 13 publications

References 77 publications

Synthesis of N,N‐Disubstituted Thiocarbamates from Thiocarbamoyl Fluorides with Alcohols/Phenols/Thiophenols/Thioalcohols Through Copper Catalysis

Synthesis of N,N‐Disubstituted Thiocarbamates from Thiocarbamoyl Fluorides with Alcohols/Phenols/Thiophenols/Thioalcohols Through Copper Catalysis

Progress of Dialkyl Azodicarboxylates in Organic Transformations

Tandem Alkylation/Michael Addition Reaction of Dithiocarbamic Acids with Alkyl γ-Bromocrotonates: Access to Functionalized 1,3-Thiazolidine-2-thiones

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