Synthesis of Arenesulfonyl Fluorides via Sulfuryl Fluoride Incorporation from Arynes

Kwon, Jay-Hyoun; Kim, Byeong Moon

doi:10.1021/acs.orglett.8b03610

Cited by 57 publications

(25 citation statements)

References 90 publications

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“…In 2018, Kim reported that zwitterion 31 could be trapped with sulfuryl fluoride to generate structurally diverse 2-amino arenesulfonyl fluoride 32d. 45 Later in 2019, Tian showed that in the presence of organic halides [CCl 4 , Nchlorosuccininmide (NCS), CBr 4 , N-bromosuccinimide (NBS), N-iodosuccinimide (NIS)], can trap zwitterionic intermediate 31 to provide the corresponding 2-chloro, 2bromo, 2-iodo aniline derivatives 32e. 46 Biju and co-workers reported that MCRs of arynes with tertiary aromatic amines and carbon dioxide formed zwitterionic intermediate 33, which could undergo either N→O alkyl or aryl group migration to generate anthranilic acid derivatives (Scheme 12).…”

Section: Account Syn Lettmentioning

confidence: 99%

Aryne-Based Multicomponent Coupling Reactions

Ghorai¹,

Lee²

2020

Synlett

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Multicomponent reactions (MCRs) constitute a powerful synthetic tool to generate a large number of small molecules with high atom economy, which thus can efficiently expand the chemical space with molecular diversity and complexity. Aryne-based MCRs offer versatile possibilities to construct functionalized arenes and benzo-fused heterocycles. Because of their electrophilic nature, arynes couple with a broad range of nucleophiles. Thus, a variety of aryne-based MCRs have been developed, the representative of which are summarized in this account.1 Introduction2 Aryne-Based Multicomponent Reactions2.1 Trapping with Isocyanides2.2 Trapping with Imines2.3 Trapping with Amines2.4 Insertion into π-Bonds2.5 Trapping with Ethers and Thioethers2.6 Trapping with Carbanions2.7 Transition-Metal-Catalyzed Approaches3 Strategies Based on Hexadehydro Diels–Alder Reaction3.1 Dihalogenation3.2 Halohydroxylation and Haloacylation3.3 Amides and Imides3.4 Quinazolines3.5 Benzocyclobutene-1,2-diimines and 3H-Indole-3-imines3.6 Other MCRs of Arynes and Isocyanides4 Conclusion

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Section: Account Syn Lettmentioning

confidence: 99%

Aryne-Based Multicomponent Coupling Reactions

Ghorai¹,

Lee²

2020

Synlett

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“…The use of sulfuryl fluoride SO2F2 for the synthesis of aryl sulfonyl fluorides was reported by the group of Kim [31]. They performed a multicomponent reaction (MCR) in-…”

Section: Sulfonyl Fluorides Synthesis From Arynesmentioning

confidence: 99%

“…The use of sulfuryl fluoride SO 2 F 2 for the synthesis of aryl sulfonyl fluorides was reported by the group of Kim [31]. They performed a multicomponent reaction (MCR) involving the in-situ generation of aryne precursors from (trimethylsilyl) phenyl trifluoromethanesulfonate, secondary amines and SO 2 F 2 .…”

Section: Sulfonyl Fluorides Synthesis From Arynesmentioning

confidence: 99%

Synthetic Routes to Arylsulfonyl Fluorides

et al. 2021

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“…(Scheme 1C). [ 10 ] Despite these advances, access to various arenesulfonyl fluoride from inexpensive and wildly available starting material by a practical and mild method is still highly desired.…”

Section: Background and Originality Contentmentioning

confidence: 99%

Arenesulfonyl Fluoride Synthesis via Copper‐free Sandmeyer‐type Fluorosulfonylation of Arenediazonium Salts

Lin

Zheng

et al. 2020

Chin. J. Chem.

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Summary of main observation and conclusion The limited availability of highly valuable arenesulfonyl fluorides seriously hinders their further application in many research fields including medicinal chemistry and chemical biological, organic synthesis, polymer preparation, etc. We report herein a mild and efficient copper‐free Sandmeyer‐type fluorosulfonylation reaction of various arenediazonium salts to prepare valuable arenesulfonyl fluorides using K2S2O5 as both a reductant and a practical sulfonyl source in combination with N‐fluorobenzenesulfonimide as an effective fluorine source. This methodology provides an attractive route to diverse important arenesulfonyl fluorides given the overall practicality and scope.

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Synthesis of Arenesulfonyl Fluorides via Sulfuryl Fluoride Incorporation from Arynes

Cited by 57 publications

References 90 publications

Aryne-Based Multicomponent Coupling Reactions

Aryne-Based Multicomponent Coupling Reactions

Synthetic Routes to Arylsulfonyl Fluorides

Arenesulfonyl Fluoride Synthesis via Copper‐free Sandmeyer‐type Fluorosulfonylation of Arenediazonium Salts

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