Title | Synthesis of Sulfilimines Enabled by Copper-Catalyzed S-Arylation of Sulfenamides |
Author | |
Corresponding Author | Kozlowski, Marisa C.; Jia, Tiezheng |
Publication Years | 2023-03-01
|
DOI | |
Source Title | |
ISSN | 0002-7863
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EISSN | 1520-5126
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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
|
Important Publications | NI Journal Papers
; ESI Hot Papers
; ESI Highly Cited Papers
|
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]
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WOS Research Area | Chemistry
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WOS Subject | Chemistry, Multidisciplinary
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WOS Accession No | WOS:000953113300001
|
Publisher | |
Data Source | Web of Science
|
Citation statistics |
Cited Times [WOS]:13
|
Document Type | Journal Article |
Identifier | http://kc.sustech.edu.cn/handle/2SGJ60CL/523963 |
Department | Department 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 Affilication | Department of Chemistry; Southern University of Science and Technology |
Corresponding Author Affilication | Department 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.
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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.
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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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