Nickel-Catalyzed C-S Bond Formation via Decarbonylative Thioetherification of Esters, Amides and Intramolecular Recombination Fragment Coupling of Thioesters

Handle URI:
http://hdl.handle.net/10754/626876
Title:
Nickel-Catalyzed C-S Bond Formation via Decarbonylative Thioetherification of Esters, Amides and Intramolecular Recombination Fragment Coupling of Thioesters
Authors:
Lee, Shao-Chi; Liao, Hsuan-Hung; Chatupheeraphat, Adisak; Rueping, Magnus ( 0000-0003-4580-5227 )
Abstract:
A nickel catalyzed cross-coupling protocol for the straightforward C-S bond formation has been developed. Various mercaptans and a wide range of ester and amide substrates bearing various substituents were tolerated in this process which afforded products in good to excellent yields. Furthermore, an intramolecular protocol for the synthesis of thioethers starting from thioesters has been developed. The utility of this protocol has been demonstrated in the synthesis of benzothiophene on the bench top.
KAUST Department:
Physical Sciences and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)
Citation:
Lee S-C, Liao H-H, Chatupheeraphat A, Rueping M (2018) Nickel-Catalyzed C-S Bond Formation via Decarbonylative Thioetherification of Esters, Amides and Intramolecular Recombination Fragment Coupling of Thioesters. Chemistry - A European Journal. Available: http://dx.doi.org/10.1002/chem.201705842.
Publisher:
Wiley-Blackwell
Journal:
Chemistry - A European Journal
KAUST Grant Number:
URF/1/3030-01
Issue Date:
15-Jan-2018
DOI:
10.1002/chem.201705842
Type:
Article
ISSN:
0947-6539
Sponsors:
H.-H. Liao gratefully acknowledges the DAAD for doctoral fellowship. This research was supported by the KAUST Office of Sponsored Research under Award No. URF/1/3030-01.
Additional Links:
http://onlinelibrary.wiley.com/doi/10.1002/chem.201705842/abstract
Appears in Collections:
Articles; Physical Sciences and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)

Full metadata record

DC FieldValue Language
dc.contributor.authorLee, Shao-Chien
dc.contributor.authorLiao, Hsuan-Hungen
dc.contributor.authorChatupheeraphat, Adisaken
dc.contributor.authorRueping, Magnusen
dc.date.accessioned2018-01-28T07:01:37Z-
dc.date.available2018-01-28T07:01:37Z-
dc.date.issued2018-01-15en
dc.identifier.citationLee S-C, Liao H-H, Chatupheeraphat A, Rueping M (2018) Nickel-Catalyzed C-S Bond Formation via Decarbonylative Thioetherification of Esters, Amides and Intramolecular Recombination Fragment Coupling of Thioesters. Chemistry - A European Journal. Available: http://dx.doi.org/10.1002/chem.201705842.en
dc.identifier.issn0947-6539en
dc.identifier.doi10.1002/chem.201705842en
dc.identifier.urihttp://hdl.handle.net/10754/626876-
dc.description.abstractA nickel catalyzed cross-coupling protocol for the straightforward C-S bond formation has been developed. Various mercaptans and a wide range of ester and amide substrates bearing various substituents were tolerated in this process which afforded products in good to excellent yields. Furthermore, an intramolecular protocol for the synthesis of thioethers starting from thioesters has been developed. The utility of this protocol has been demonstrated in the synthesis of benzothiophene on the bench top.en
dc.description.sponsorshipH.-H. Liao gratefully acknowledges the DAAD for doctoral fellowship. This research was supported by the KAUST Office of Sponsored Research under Award No. URF/1/3030-01.en
dc.publisherWiley-Blackwellen
dc.relation.urlhttp://onlinelibrary.wiley.com/doi/10.1002/chem.201705842/abstracten
dc.rightsThis is the peer reviewed version of the following article: Nickel-Catalyzed C-S Bond Formation via Decarbonylative Thioetherification of Esters, Amides and Intramolecular Recombination Fragment Coupling of Thioesters, which has been published in final form at http://doi.org/10.1002/chem.201705842. This article may be used for non-commercial purposes in accordance With Wiley Terms and Conditions for self-archiving.en
dc.titleNickel-Catalyzed C-S Bond Formation via Decarbonylative Thioetherification of Esters, Amides and Intramolecular Recombination Fragment Coupling of Thioestersen
dc.typeArticleen
dc.contributor.departmentPhysical Sciences and Engineering (PSE) Divisionen
dc.contributor.departmentChemical Science Programen
dc.contributor.departmentKAUST Catalysis Center (KCC)en
dc.identifier.journalChemistry - A European Journalen
dc.eprint.versionPost-printen
dc.contributor.institutionRWTH Aachen; Institure of Organic Chemistry; Landoltweg 1 52074 Aachen GERMANYen
kaust.authorRueping, Magnusen
kaust.grant.numberURF/1/3030-01en
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