Synthesis of 3-(Bromomethylene)isobenzofuran-1(3H)-ones through regioselective 5-exo-dig bromocyclization of 2-alkynylbenzoic acids

Zheng, Yan-Nan; Liu, Mengli; Qiu, Guanyinsheng; Xie, Wei; Wu, Jie

doi:10.1016/j.tet.2018.11.045

Cited by 37 publications

(5 citation statements)

References 62 publications

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“…In 2019, the group of Wu published a regioselective bromocyclization of 2‐alkynylbenzoic acids (Scheme 13). [17] The reaction proceeds smoothly in presence of oxone® and tetrabutylammonium bromide to afford a large scope of ylidenephthalide as single E isomers with good yields. The mechanistic pathway was not clearly established but could involves a radical specie.…”

Section: Intramolecular Cyclizationsmentioning

confidence: 99%

Preparation of 3‐Alkylidenephthalides: Recent Advances

et al. 2022

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3-Alkylidenephthalides represent an important class of natural compounds which are also valuable synthetic precursors for the preparation of phthalides. While recent reviews reported the great interest of the phthalides in the field of medicinal chemistry, few reports are mentioning the recent progress for the synthesis of their unsaturated homologous in the position 3. So, the aim of this report is to present the latest progresses (since 2010 and until 2021) in the synthesis of 3-alkylidenephtalides.www.eurjoc.org

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Section: Intramolecular Cyclizationsmentioning

confidence: 99%

Preparation of 3‐Alkylidenephthalides: Recent Advances

et al. 2022

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“…Finally, after a radical hydrogen abstraction, the intermediate B is converted to the isocoumarin 53 (Scheme 34). The system TBAB/Oxone was also employed in the 5-exo-dig bromocyclization of 2-alkynylbenzoic acids 52, aiming the synthesis of 3-(bromomethylene)isobenzofuran-1(3H)-ones 54, employing overstoichiometric amounts of TBAB (1.5 equiv) (Scheme 35) [39]. A total of fifteen 3-(bromomethylene)isobenzofuran-1(3H)-ones 54 were obtained in mod-erate to very good yields, starting from alkynyl-substituted substrate 52 bearing electronrich and -deficient aryl groups.…”

Section: Oxygen-containing Heterocyclesmentioning

confidence: 99%

Recent Advances in the Oxone-Mediated Synthesis of Heterocyclic Compounds

et al. 2021

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Oxone is a commercially available oxidant, composed of a mixture of three inorganic species, being the potassium peroxymonosulfate (KHSO5) the reactive one. Over the past few decades, this cheap and environmentally friendly oxidant has become a powerful tool in organic synthesis, being extensively employed to mediate the construction of a plethora of important compounds. This review summarizes the recent advances in the Oxone-mediated synthesis of N-, O- and chalcogen-containing heterocyclic compounds, through a wide diversity of reactions, starting from several kinds of substrate, highlighting the main synthetic differences, advantages, the scope and limitations.

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“…[5l] Generally, the sulfur dioxide surrogates of inorganic sulfites and DABCO·(SO 2 ) 2 , (1,4‐diazabicyclo[2.2.2]octane‐sulfur dioxide) are used instead of gaseous sulfur dioxide, due to its toxic property and handling problem with the gaseous sulfur dioxide. [5g] This approach would provide diverse sulfones and sulfonamides avoiding the utilization of pre‐installed sulfonyl compounds or odorous thiol substrates , . Especially, the convenient, cheap and easily available inorganic sulfites such as potassium/sodium metabisulfite could be used as the source of sulfur dioxide during the reaction process .…”

Section: Introductionmentioning

confidence: 99%

Photoinduced Sulfonylation Reactions through the Insertion of Sulfur Dioxide

Xie

et al. 2019

Eur J Org Chem

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Recent advances in the photoinduced sulfonylation reactions through the insertion of sulfur dioxide are summarized. Among the approaches developed in the sulfonylation reactions, the insertion of sulfur dioxide via radical process can be accomplished with the assistance of photoredox catalysis in the presence of visible light or under ultraviolet irradiation, depending the substrates used in the reactions. Under ultraviolet irradiation, the conversion can be completed under metal‐ and additive‐free conditions. It is noteworthy that alkyl halides possessing eliminable β‐hydrogen atom are effective as alkyl radical precursors with the insertion of sulfur dioxide. Two parts, according to the photoinduced reaction pathways, are introduced: (a) photo‐initiated formation of radical with the subsequent capture of sulfur dioxide; (b) photo‐assisted single electron transfer (SET) after insertion of sulfur dioxide. During the transformation, an oxidative or reductive single electron transfer would occur under visible light photoredox catalysis.

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Synthesis of 3-(Bromomethylene)isobenzofuran-1(3H)-ones through regioselective 5-exo-dig bromocyclization of 2-alkynylbenzoic acids

Cited by 37 publications

References 62 publications

Preparation of 3‐Alkylidenephthalides: Recent Advances

Preparation of 3‐Alkylidenephthalides: Recent Advances

Recent Advances in the Oxone-Mediated Synthesis of Heterocyclic Compounds

Photoinduced Sulfonylation Reactions through the Insertion of Sulfur Dioxide

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