中文版 | English
Title

Synthesis of Sulfilimines Enabled by Copper-Catalyzed S-Arylation of Sulfenamides

Author
Corresponding AuthorKozlowski, Marisa C.; Jia, Tiezheng
Publication Years
2023-03-01
DOI
Source Title
ISSN
0002-7863
EISSN
1520-5126
Abstract
Herein, an unprecedented synthetic route to sulfilimines via a copper catalyzed Chan-Lam-type coupling of sulfenamides is presented. A key to success in this novel transformation is the chemoselective S-arylation of S(II) sulfenamides to form S(IV) sulfilimines, overriding the competitive, and more thermodynamically favored, C-N bond formation that does not require a change in the sulfur oxidation state. Computations reveal that the selectivity arises from a selective transmetallation event where bidentate sulfenamide coordination through the sulfur and oxygen atoms favors the S-arylation pathway. The mild and environmentally benign catalytic conditions enable broad functional group compatibility, allowing a variety of diaryl or alkyl aryl sulfilimines to be efficiently prepared. The Chan-Lam coupling procedure could also tolerate alkenylboronic acids as coupling partners to afford alkenyl aryl sulfilimines, a class of scaffolds that cannot be directly synthesized via conventional imination strategies. The benzoyl-protecting groups could be conveniently removed from the product, which, in turn, could be readily transformed into several S(IV) and S(VI) derivatives.
URL[Source Record]
Indexed By
Language
English
SUSTech Authorship
Corresponding
Funding Project
Guangdong-Joint Foundation of Shenzhen["2021B1515120046","2022B1515120075"] ; Natural Science Foundation of Guangdong Province[2022A1515011770] ; Science and Technology Innovation Commission of Shenzhen Municipality["JCYJ20220818101404010","20220815113214003"] ; Guangdong Provincial Key Laboratory of Catalysis[2020B121201002] ; NIH[R35 GM131902] ; null[22061031]
WOS Research Area
Chemistry
WOS Subject
Chemistry, Multidisciplinary
WOS Accession No
WOS:000953113300001
Publisher
Data Source
Web of Science
Citation statistics
Cited Times [WOS]:5
Document TypeJournal Article
Identifierhttp://kc.sustech.edu.cn/handle/2SGJ60CL/523963
DepartmentDepartment of Chemistry
Affiliation
1.Harbin Inst Technol, Sch Chem & Chem Engn, Harbin 150001, Peoples R China
2.Southern Univ Sci & Technol, Res Ctr Chem Biol & Om Anal, Dept Chem, Shenzhen 518055, Guangdong, Peoples R China
3.Southern Univ Sci & Technol, Guangdong Prov Key Lab Catalysis, Shenzhen 518055, Guangdong, Peoples R China
4.Univ Penn, Dept Chem, Roy & Diana Vagelos Labs, Philadelphia, PA 19104 USA
5.Inner Mongolia Univ, Sch Chem & Chem Engn, P, R China, Hohhot 010021, Peoples R China
6.Nankai Univ, State Key Lab Elemento Organ Chem, Tianjin 300071, Peoples R China
First Author AffilicationDepartment of Chemistry;  Southern University of Science and Technology
Corresponding Author AffilicationDepartment of Chemistry;  Southern University of Science and Technology
Recommended Citation
GB/T 7714
Liang, Qingjin,Wells, Lucille A.,Han, Kaiming,et al. Synthesis of Sulfilimines Enabled by Copper-Catalyzed S-Arylation of Sulfenamides[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,2023.
APA
Liang, Qingjin,Wells, Lucille A.,Han, Kaiming,Chen, Shufeng,Kozlowski, Marisa C.,&Jia, Tiezheng.(2023).Synthesis of Sulfilimines Enabled by Copper-Catalyzed S-Arylation of Sulfenamides.JOURNAL OF THE AMERICAN CHEMICAL SOCIETY.
MLA
Liang, Qingjin,et al."Synthesis of Sulfilimines Enabled by Copper-Catalyzed S-Arylation of Sulfenamides".JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2023).
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