TFA-promoted sulfonation/cascade cyclization of 2-propynolphenols with sodium sulfinates to 4-sulfonyl 2<i>H</i>-chromenes under metal-free conditions

Yang, Tao; Kou, Peihao; Jin, Fengyan; Song, Xian‐Rong; Bai, Jiang; Ding, Haixin; Liang, Yong‐Min

doi:10.1039/c9qo00712a

Cited by 20 publications

(10 citation statements)

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“…For example, various 4‐sulfonyl 2 H ‐chromenes 90 were successfully prepared by using sodium sulfinates as nucleophiles in the presence of TFA [51a] . This reaction avoided the use of oxidant or photo‐radical inducer, and a wide variety of functional groups were tolerated.…”

Section: Reactions Involving O S‐nucleophiles To Capture Allenyl Carmentioning

confidence: 99%

Recent Advances in the Synthesis of Heterocyclics via Cascade Cyclization of Propargylic Alcohols

2020

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Heterocyclic compounds are important organic compounds and have emerged as key scaffolds in numerous drugs, natural products, vitamins, biologically and pharmaceutically active compounds. Over the past few decades, the development of versatile methodologies employing propargylic alcohols as synthons for the construction of heterocyclic skeletons has attracted great attention from synthetic chemists. In this review, recent developments in the cascade cyclization of propargylic alcohols with diverse nucleophiles to construct heterocyclic compounds are summarized. According to the types of nucleophiles, these reactions can be divided into four categories: 1) Reactions involving C‐nucleophiles to capture allenyl carbocation; 2) Reactions involving O, S‐nucleophiles to capture allenyl carbocation; 3) Reactions involving N, P‐nucleophiles to capture allenyl carbocation; 4) Reactions involving halo‐nucleophiles to capture allenyl carbocation.

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Section: Reactions Involving O S‐nucleophiles To Capture Allenyl Carmentioning

confidence: 99%

Recent Advances in the Synthesis of Heterocyclics via Cascade Cyclization of Propargylic Alcohols

2020

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“…The TFA-promoted ring-closing sulfonylation of 2-propynolphenols with sodium sulfinates was developed by Liang and co-workers for the synthesis of 4-sulfonyl 2 H -chromenes under mild conditions ( Scheme 203 ). 310 The reaction occurred by the nucleophilic addition of sulfinates to the allylene carbocation intermediate followed by a 6- endo -trig pathway. Various symmetrical and unsymmetrical tertiary propargylic alcohols could be transformed into the desired products in moderate to high yields.…”

Section: Applications Of Sodium Sulfinatesmentioning

confidence: 99%

Synthesis and applications of sodium sulfinates (RSO₂Na): a powerful building block for the synthesis of organosulfur compounds

2021

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“…4‐Sulfonyl‐2 H ‐chromenes were obtained by cascade cyclization of 2‐propynolphenols and sodium sulfinates in the presence of TFA in nitromethane, products yields were 61–89% [291] …”

Section: Sulfonylation Followed By Cyclizationmentioning

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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TFA-promoted sulfonation/cascade cyclization of 2-propynolphenols with sodium sulfinates to 4-sulfonyl 2H-chromenes under metal-free conditions

Abstract: A novel, efficient and metal-free cascade sulfonylation/cyclization of 2-propynolphenols with commercially available sodium sulfinates was developed for the synthesis of 4-sulfonyl 2H-chromenes under mild conditions.

Cited by 20 publications

References 53 publications

Recent Advances in the Synthesis of Heterocyclics via Cascade Cyclization of Propargylic Alcohols

Recent Advances in the Synthesis of Heterocyclics via Cascade Cyclization of Propargylic Alcohols

Synthesis and applications of sodium sulfinates (RSO₂Na): a powerful building block for the synthesis of organosulfur compounds

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

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TFA-promoted sulfonation/cascade cyclization of 2-propynolphenols with sodium sulfinates to 4-sulfonyl 2H-chromenes under metal-free conditions

Abstract: A novel, efficient and metal-free cascade sulfonylation/cyclization of 2-propynolphenols with commercially available sodium sulfinates was developed for the synthesis of 4-sulfonyl 2H-chromenes under mild conditions.

Cited by 20 publications

References 53 publications

Recent Advances in the Synthesis of Heterocyclics via Cascade Cyclization of Propargylic Alcohols

Recent Advances in the Synthesis of Heterocyclics via Cascade Cyclization of Propargylic Alcohols

Synthesis and applications of sodium sulfinates (RSO2Na): a powerful building block for the synthesis of organosulfur compounds

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

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Synthesis and applications of sodium sulfinates (RSO₂Na): a powerful building block for the synthesis of organosulfur compounds