Palladium‐Catalyzed Amination of Aryl Sulfides with Anilines

Sugahara, Tomohiro; Murakami, Kei; Yorimitsu, Hideki; Osuka, Atsuhiro

doi:10.1002/anie.201404355

Cited by 105 publications

(39 citation statements)

References 102 publications

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“…In line with our interest in catalytic C−S bond transformations,,– we herein report that simple insertion of tert ‐butyl isocyanide into the C−S bonds of heteroaryl sulfides proceeded by means of a palladium catalyst to provide thioimidates (Scheme e). The resulting thioimidates could be easily converted into the corresponding thioesters by acidic hydrolysis.…”

Section: Methodssupporting

confidence: 56%

Palladium‐Catalyzed Insertion of Isocyanides into the C−S Bonds of Heteroaryl Sulfides

2018

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Insertion of tert‐butyl isocyanide into the C(sp2)−S bonds of heteroaryl sulfides is catalyzed by a palladium diphosphine complex. Thioimidates generated through this reaction could be readily hydrolyzed under acidic conditions to yield the corresponding thioesters, which are of synthetic use. This insertion is useful because starting heteroaryl sulfides were readily prepared by either conventional ways or through sulfur‐specific extended Pummerer reactions.

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Section: Methodssupporting

confidence: 56%

Palladium‐Catalyzed Insertion of Isocyanides into the C−S Bonds of Heteroaryl Sulfides

2018

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“…Once again, NHC ligands were found to play a key role in the amination reaction of aryl sul des. 24 Treatment of methyl phenyl sul de (34) with p toluidine (35a) by means of IPr ligated Pd NHC precatalysts gave the corresponding aminated product 36a in good yields (Table 4, entries 2 6). Especially, SingaCycle A3 proved to be the optimal precatalyst, and nally, a 91% yield of 36a was isolated in the presence of KN(SiMe 3 ) 2 as base in dioxane at 100…”

Section: With Aminesmentioning

confidence: 99%

Cross-coupling of Aryl Sulfides Powered by <i><b>N</b></i>-Heterocyclic Carbene Ligands

Gao¹,

Otsuka²,

Baralle³

et al. 2016

J. Synth. Org. Chem. Jpn.

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Cross coupling reactions of aryl sul des are more dif cult than they look. We have disclosed that transition metal NHC complexes allow us to ef ciently use a wide range of aryl sul des as electrophilic coupling partners in various cross coupling reactions and have thus signi cantly expanded the scope of aryl suldes available for the cross coupling technology. Newly introduced nucleophilic partners include arylzinc reagents, Grignard reagents such as alkynylmagnesium species, amines, ketimines, and diborons to achieve Negishi type coupling, Kumada Tamao Corriu type coupling, Buchwald Hartwig type amination, Buchwald Hartwig Miura type carbonyl α arylation, and Miyaura type borylation, respectively. These cross coupling reactions are particularly advantageous when combined with sulfur speci c transformations to prepare organosulfur substrates. Through the development of catalytic transformations of C S bonds, sulfur based organic synthesis has come to complement conventional halogen based organic methodology.

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“…The development of new catalytic reactions of C–S bonds would be an important challenge, since C–S bonds are found widely in organic feedstocks, synthetic intermediates, and useful products. As a part of our recent research into catalytic C–S bond cleavage,11 we reported the first palladium‐catalyzed amination of aryl sulfides (Scheme ) 11c. A palladium–NHC (N‐heterocyclic carbene) precatalyst, SingaCycle‐A3, showed excellent reactivity for C–S bond cleavage.…”

Section: Introductionmentioning

confidence: 99%

Palladium‐Catalyzed Amination of Aryl Sulfides with Aliphatic Amines

2015

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Conditions for the palladium–NHC‐catalyzed amination of aryl sulfides with aliphatic as well as aromatic amines were established. The KHMDS‐mediated amination of heteroaryl sulfides could proceed without palladium. Based on the distinct difference in reactivity of C–Br and C–S bonds, a sequential amination of bromothioanisole can take place to install two different alkylamino groups onto the aromatic ring in one pot.

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Palladium‐Catalyzed Amination of Aryl Sulfides with Anilines

Cited by 105 publications

References 102 publications

Palladium‐Catalyzed Insertion of Isocyanides into the C−S Bonds of Heteroaryl Sulfides

Palladium‐Catalyzed Insertion of Isocyanides into the C−S Bonds of Heteroaryl Sulfides

Cross-coupling of Aryl Sulfides Powered by <i><b>N</b></i>-Heterocyclic Carbene Ligands

Palladium‐Catalyzed Amination of Aryl Sulfides with Aliphatic Amines

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