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Title: Mild and Chemoselective Thioacylation of Amines Enabled by the Nucleophilic Activation of Elemental Sulfur
Authors: Saito, Masato
Murakami, Sho
Nanjo, Takeshi  kyouindb  KAKEN_id  orcid https://orcid.org/0000-0002-5679-6701 (unconfirmed)
Kobayashi, Yusuke
Takemoto, Yoshiji  kyouindb  KAKEN_id  orcid https://orcid.org/0000-0003-1375-3821 (unconfirmed)
Author's alias: 村上, 翔
南條, 毅
小林, 祐輔
竹本, 佳司
Issue Date: 6-May-2020
Publisher: American Chemical Society (ACS)
Journal title: Journal of the American Chemical Society
Volume: 142
Issue: 18
Start page: 8130
End page: 8135
Abstract: A mild and chemoselective method for the thioacylation of amines using α-keto acids and elemental sulfur has been developed. The key to the success of this transformation is the nucleophilic activation of elemental sulfur by thiols such as 1-dodecanethiol. A variety of functional groups, including unprotected hydroxyl, carboxyl, amide, sulfide, and tertiary amine moieties, are tolerated under the applied reaction conditions. To demonstrate the advantages of this method compared with conventional O–S exchange reactions using Lawesson’s reagent or P2S5, thioamide moieties were introduced site-specifically into biologically active compounds.
Rights: This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of the American Chemical Society, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/jacs.0c03256.
The full-text file will be made open to the public on 21 April 2021 in accordance with publisher's 'Terms and Conditions for Self-Archiving'.
This is not the published version. Please cite only the published version.
この論文は出版社版でありません。引用の際には出版社版をご確認ご利用ください。
URI: http://hdl.handle.net/2433/253551
DOI(Published Version): 10.1021/jacs.0c03256
PubMed ID: 32315161
Appears in Collections:Journal Articles

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