SVI-C Linkage for Allylsulfonximines via BF3-Mediated Allylation

Daming Zeng; Suqin Zhao; Wei Ping Deng; Xuefeng Jiang

doi:10.1021/acs.orglett.3c01902

S^VI-C Linkage for Allylsulfonximines via BF₃-Mediated Allylation

Daming Zeng, Suqin Zhao, Wei Ping Deng, Xuefeng Jiang

School of Chemistry and Molecular Engineering

Research output: Contribution to journal › Article › peer-review

6 Scopus citations

Abstract

A SuFEx linkage reaction between sulfonimidoyl fluoride and allyltrimethylsilane was achieved for the construction of N-modified allylsulfoximines in minutes with BF₃ as a nonmetal difunctional activator enabling the activation of both S-F and C-Si bonds to forge the S-C_allyl (sp³) bond swiftly. Mechanistic studies and DFT calculations indicated that the linkage was initiated with the activation of sulfonimidoyl fluoride and then followed with the transfer of the fluoride anion to the TMS group.

Original language	English
Pages (from-to)	5591-5596
Number of pages	6
Journal	Organic Letters
Volume	25
Issue number	30
DOIs	https://doi.org/10.1021/acs.orglett.3c01902
State	Published - 4 Aug 2023

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title = "SVI-C Linkage for Allylsulfonximines via BF3-Mediated Allylation",

abstract = "A SuFEx linkage reaction between sulfonimidoyl fluoride and allyltrimethylsilane was achieved for the construction of N-modified allylsulfoximines in minutes with BF3 as a nonmetal difunctional activator enabling the activation of both S-F and C-Si bonds to forge the S-Callyl (sp3) bond swiftly. Mechanistic studies and DFT calculations indicated that the linkage was initiated with the activation of sulfonimidoyl fluoride and then followed with the transfer of the fluoride anion to the TMS group.",

author = "Daming Zeng and Suqin Zhao and Deng, \{Wei Ping\} and Xuefeng Jiang",

note = "Publisher Copyright: {\textcopyright} 2023 American Chemical Society.",

year = "2023",

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doi = "10.1021/acs.orglett.3c01902",

language = "英语",

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journal = "Organic Letters",

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TY - JOUR

T1 - SVI-C Linkage for Allylsulfonximines via BF3-Mediated Allylation

AU - Zeng, Daming

AU - Zhao, Suqin

AU - Deng, Wei Ping

AU - Jiang, Xuefeng

PY - 2023/8/4

Y1 - 2023/8/4

N2 - A SuFEx linkage reaction between sulfonimidoyl fluoride and allyltrimethylsilane was achieved for the construction of N-modified allylsulfoximines in minutes with BF3 as a nonmetal difunctional activator enabling the activation of both S-F and C-Si bonds to forge the S-Callyl (sp3) bond swiftly. Mechanistic studies and DFT calculations indicated that the linkage was initiated with the activation of sulfonimidoyl fluoride and then followed with the transfer of the fluoride anion to the TMS group.

AB - A SuFEx linkage reaction between sulfonimidoyl fluoride and allyltrimethylsilane was achieved for the construction of N-modified allylsulfoximines in minutes with BF3 as a nonmetal difunctional activator enabling the activation of both S-F and C-Si bonds to forge the S-Callyl (sp3) bond swiftly. Mechanistic studies and DFT calculations indicated that the linkage was initiated with the activation of sulfonimidoyl fluoride and then followed with the transfer of the fluoride anion to the TMS group.

UR - https://www.scopus.com/pages/publications/85166481989

U2 - 10.1021/acs.orglett.3c01902

DO - 10.1021/acs.orglett.3c01902

M3 - 文章

C2 - 37481737

AN - SCOPUS:85166481989

SN - 1523-7060

VL - 25

SP - 5591

EP - 5596

JO - Organic Letters

JF - Organic Letters

IS - 30

ER -

S^VI-C Linkage for Allylsulfonximines via BF₃-Mediated Allylation

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