TBN-mediated regio- and stereoselective sulfonylation &amp; oximation (oximosulfonylation) of alkynes with sulfonyl hydrazines in EtOH/H<sub>2</sub>O

Wang, Bin; Yan, Zicong; Liu, Liyan; Wang, Jiawei; Zha, Zhenggen

doi:10.1039/c8gc02708k

Cited by 38 publications

(21 citation statements)

References 127 publications

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“…The benzenesulfonyl hydrazide bearing electron‐withdrawing groups gave higher yields as compared to electron‐donating groups. Whereas, an opposite trend in yield pattern was observed in the case of phenylacetylene …”

Section: Outlines Of the Reactions Involving Tbnmentioning

confidence: 79%

“…Whereas, an opposite trend in yield pattern was observed in the case of phenylacetylene. [112] Formation of CÀNb ond via CÀHa ctivation and functionalization are still in demandb ecause of their industrial importance. In 2015, Lu group reportedaCu-catalyzed synthesis of aromatico ximes (112)f rom methylarenes( 111)u sing NHPI (Nhydroxypthalmide) as the additive and TBN as an oxidant.…”

Section: Oximationmentioning

confidence: 99%

“…In the first step Cu(OAc) 2 is oxidized by NHPI (N-hydroxypthalamide) to form an N-oxy radical PINO (phthalimide N-oxy), then this N-oxy radical abstracts a hydrogena tom from methylarene (I)t og enerate benzylic radical (II)a nd recovers the NHPI. Simultaneously, benzylic radical (II)r eacts with TBN to form an intermediate (III)w hich on tautomerization gives corresponding oxime (112). The generated tBuO radical easily abstracts hydrogen atom from NHPI to form PINO andmaintains the catalytic cycle (Scheme 83).…”

Section: Oximationmentioning

confidence: 99%

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tert‐Butyl Nitrite (TBN), a Multitasking Reagent in Organic Synthesis

Dahiya

Sahoo

Alam

et al. 2019

Chemistry An Asian Journal

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The upsurge interesti nt he development of efficient methodologies for the constructiono fn itrogen-containing frameworks via the use of expedient reagents have been creating ar enaissance in contemporary organic chemistry.I nt his perspective, tertbutyl nitrite (TBN) is an emerging building block. Due to its uniques tructuralf eatures, it shows differential reactivity under different reaction conditions. These diverse reactivities have resulted in the construction of ad iverse array of complex N-containing molecules. The primary objective of the presentr eview is to bring the latest findings of TBN in terms of its applications in reactions (oxidation, diazotization, nitrosation, nitration, oximation, N-synthon, and miscellaneous reactions) into the limelight.F or simplicity and brevity,r eactions in each section are explained with the mechanism of formation and selected examples are given.Scheme1.Differential reactivity of TBN. 4455 MinireviewScheme4.Visible-light-promoted synthesis of selenide ethers.Scheme5.Proposed mechanism for visible-light-promoted synthesis of selenide ethers.Scheme6.TBN-mediated synthesis of selenide ethers.Scheme7.Metal-free synthesis of 4-carbonylquinolines.Scheme8.Proposed mechanism for synthesis of 4-carbonylquinolines.Scheme9.TBN-mediated demethylative borylation of methylarenes.Scheme10. Plausible mechanism for demethylative borylation of methylarenes.Scheme11. Trifluoromethylation of various aromatic amine substrates.Scheme12. Copper-catalyzed isoperfluoropropylation of anilines.Scheme13. Plausible mechanism for Cu-catalyzed isoperfluoropropylation of anilines.Scheme14. TBN-mediateddiazotizative allylation of aromatic amines.Scheme15. Oxidativecyanomethylationo fa lkenes via CÀHb ond activation.Scheme16. TBN-mediatedand Cu-catalyzedsynthesis of thioether.

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Section: Outlines Of the Reactions Involving Tbnmentioning

confidence: 79%

Section: Oximationmentioning

confidence: 99%

Section: Oximationmentioning

confidence: 99%

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tert‐Butyl Nitrite (TBN), a Multitasking Reagent in Organic Synthesis

Dahiya

Sahoo

Alam

et al. 2019

Chemistry An Asian Journal

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“…Yields of the target products were 20-80%. [94] Conducting the reaction in NMPÀ H 2 O system in the presence of imidazole avoids inert atmosphere . [95] The reaction of terminal alkynes 162 with sodium sulfinates 163 in the presence of t-BuONO leads to 2,2-disulfonyl-2H-azirines 164.…”

Section: Miscellaneousmentioning

confidence: 99%

Oxidative Sulfonylation of Multiple Carbon‐Carbon bonds with Sulfonyl Hydrazides, Sulfinic Acids and their Salts

et al. 2020

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Oxidative coupling methodology is widely applied for the formation of carbon-carbon and carbon-heteroatom bonds. This review focuses on methods for oxidative sulfonylation of multiple bonds involving sulfonyl hydrazides, sulfinic acids and their salts as sulfonylation reagents. Under oxidative conditions, they generate sulfonyl radicals, trapped by multiple carbon-carbon bonds resulting in a variety of SO 2-containing products: mainly, vinyl and alkynyl sulfones, hydroxy-, keto, and halo-substituted sulfones, sulfonylated derivatives of carbo-and heterocycles. This exhaustive review summarizes 321 references from 1996 to 2020 with the specialization of the studies of the last five years, and is divided into the chapters according to the classes of compounds being sulfonylated.

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“…In 2019, the TBN-mediated regio-and stereoselective sulfonylation/oximation of alkynes with sulfonyl hydrazines was realized by Wang group. [122] This strategy features broad substrate scope, environmentally benign solvent, and transition metal free. Sulfonyl radical was suggested in the reaction.…”

Section: Sulfonylation With Alkynesmentioning

confidence: 99%

Recent Progress in Sulfonylation via Radical Reaction with Sodium Sulfinates, Sulfinic Acids, Sulfonyl Chlorides or Sulfonyl Hydrazides

et al. 2020

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Sodium sulfinates, sulfinic acids, sulfonyl chlorides and sulfonyl hydrazides as readily available and efficient sulfonylation reagents have been extensively explored in recent years. Sulfonyl radical can be generated from these sulfonyl reagents via different methods, then the sulfonyl radical could react with various substrates via different pathways to afford the corresponding products. In this review, we will summarize the progress in sulfonylation via radical reaction using sodium sulfinates, sulfinic acids, sulfonyl chlorides and sulfonyl hydrazides in recent three years. In terms of the different sulfonylation reagents, we classify these sulfonylation reactions into four types: 1.

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TBN-mediated regio- and stereoselective sulfonylation & oximation (oximosulfonylation) of alkynes with sulfonyl hydrazines in EtOH/H₂O

Abstract: A difunctionalization of alkynes cascade reaction was developed to generate α-sulfonylethanone oximes in environmentally benign EtOH/H2O.

Cited by 38 publications

References 127 publications

tert‐Butyl Nitrite (TBN), a Multitasking Reagent in Organic Synthesis

tert‐Butyl Nitrite (TBN), a Multitasking Reagent in Organic Synthesis

Oxidative Sulfonylation of Multiple Carbon‐Carbon bonds with Sulfonyl Hydrazides, Sulfinic Acids and their Salts

Recent Progress in Sulfonylation via Radical Reaction with Sodium Sulfinates, Sulfinic Acids, Sulfonyl Chlorides or Sulfonyl Hydrazides

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TBN-mediated regio- and stereoselective sulfonylation & oximation (oximosulfonylation) of alkynes with sulfonyl hydrazines in EtOH/H2O

Abstract: A difunctionalization of alkynes cascade reaction was developed to generate α-sulfonylethanone oximes in environmentally benign EtOH/H2O.

Cited by 38 publications

References 127 publications

tert‐Butyl Nitrite (TBN), a Multitasking Reagent in Organic Synthesis

tert‐Butyl Nitrite (TBN), a Multitasking Reagent in Organic Synthesis

Oxidative Sulfonylation of Multiple Carbon‐Carbon bonds with Sulfonyl Hydrazides, Sulfinic Acids and their Salts

Recent Progress in Sulfonylation via Radical Reaction with Sodium Sulfinates, Sulfinic Acids, Sulfonyl Chlorides or Sulfonyl Hydrazides

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TBN-mediated regio- and stereoselective sulfonylation & oximation (oximosulfonylation) of alkynes with sulfonyl hydrazines in EtOH/H₂O