Catalyst-free radical fluorination of sulfonyl hydrazides in water

Tang, Lin; Yang, Yu; Wen, Lixian; Xing-kun, Yang; Wang, Zhiyong

doi:10.1039/c5gc02755a

Cited by 98 publications

(39 citation statements)

References 67 publications

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“…Traditional approaches mainly relied on nucleophilic substitution of sulfonyl chlorides with the fluoride anion, which required strict anhydrous conditions. Wang and co‐workers used Selectfluor as oxidant and fluoride source in an aqueous fluorination of sulfonyl hydrazides (Eq. 41‐1).…”

Section: Sulfonyl Radiacls‐mediated Reactionsmentioning

confidence: 99%

“…In our opinion, a summary classified by crucial intermediates will do much to help the application of diverse methodologies. As shown in Scheme , our review is based on ten categories: (1) sulfonyl radiacls; (2) thiosulfonates; (3) ArS . radicals; (4) sulfur‐centered anions; (5/6) metallo‐organic compounds with or without sulfonyl moiety; (7/8) electrophilic RSX or RS‐DBU intermediates; (9) nucleophilic hydrazines; (10) sulfonyl hydrazides as diazene or sulfinic acid surrogate.…”

Section: Introductionmentioning

confidence: 99%

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Sulfonyl Hydrazides in Organic Synthesis: A Review of Recent Studies

et al. 2020

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Sulfonyl hydrazides are widely used as organic reagents. Advances in the past decade are summarized in the following categories by key intermediates: (1) [RO2S.]; (2) RO2SSR; (3) [ArS.]; (4) [RO2S−]; (5) RSO2‐[Metal] species; (6) Ar‐[Metal] species; (7) RSX; (8) RS‐DBU; (9) nucleophilic amino group; (10) sulfonyl hydrazides as diazene or sulfinic acid surrogate. Reactions with alkenes, alkynes, aldehydes, alcohols, thiophenol, Grignard reagents, among others, are discussed. We hope this review will promote future research in this area.

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Section: Sulfonyl Radiacls‐mediated Reactionsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Sulfonyl Hydrazides in Organic Synthesis: A Review of Recent Studies

et al. 2020

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“…Further studies indicated that 3.0 equivalents of 1a was optimal ( Table 1, entries 17 and 18). [15] Given that water is the most easily available and nontoxic solvent in organic synthesis, [16] we chose the conditions outlinedi ne ntry 15 of Table 1a so ptimal.…”

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confidence: 99%

Heterogeneous Palladium‐Catalyzed Hydrogen‐Transfer Cyclization of Nitroacetophenones with Benzylamines: Access to C−N Bonds

et al. 2016

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The first Pd/C‐catalyzed oxidative C(sp3)−H bond amination of o‐nitroacetophenones with benzylamines or amino acids proceeding through C−N bond cleavage followed by C−N bond formation by a hydrogen‐transfer strategy was developed. These transformations proceeded smoothly in water to afford the desired quinazolines in moderate to good yields. This protocol has a broad substrate scope and good tolerance of air, offers excellent recyclability of the catalyst, and does not need any additional oxidant, ligand, or base; the combination of all of these factors give a new and practical avenue for multiple C−N bond formation. Moreover, a hot filtration experiment indicated that heterogeneous palladium nanoparticles during the reaction are the active species.

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“…There are various methods to prepare sulfonyl fluorides from different type of starting materials such as heteroaromatic thiols, sulfonic acid, sodium benzene sulfonate, sulfonyl hydrazide, bromo benzene, iodo benzene, benzenethiosulfonate, diaryl sulfides, aryl sulfonyl chlorides, and some other unconventional starting material (Figure ) . In addition, alkyl sulfonyl fluorides may be readily accessed from alkyl bromides and rongalite, or through an electrochemical process .…”

Section: Preparation Of Molecules With Sf Bondsmentioning

confidence: 99%

Sulfonyl Fluorides (SFs): More Than Click Reagents?

2018

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Sulfonyl fluoride (SF) containing substances are currently attracting enormous attention among practitioners of both chemical biology and synthetic organic chemistry. The groups of Jones and Liskamp have demonstrated the potential of sulfonyl fluorides as selective covalent inhibitors in studies related to drug discovery and chemical biology, respectively, in the last few years. The Sharpless group has extended the repertoire of “click‐reactions” to those involving sulfonyl fluorides, that is, sulfur–fluoride exchange (SuFEx), a development that quickly triggered the interest in this functional group in the community of synthetic organic chemists. In this microreview, we aim to give an account of the synthetic chemistry surrounding sulfonyl fluoride containing substances from a historical perspective to present day developments.

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Catalyst-free radical fluorination of sulfonyl hydrazides in water

Abstract: The first catalyst-free fluorination of sulfonyl hydrazides for the synthesis of sulfonyl fluorides via a free-radical process has been developed.

Cited by 98 publications

References 67 publications

Sulfonyl Hydrazides in Organic Synthesis: A Review of Recent Studies

Sulfonyl Hydrazides in Organic Synthesis: A Review of Recent Studies

Heterogeneous Palladium‐Catalyzed Hydrogen‐Transfer Cyclization of Nitroacetophenones with Benzylamines: Access to C−N Bonds

Sulfonyl Fluorides (SFs): More Than Click Reagents?

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