Aryne Chemistry: Generation Methods and Reactions Incorporating Multiple Arynes

Chemical Reviews, Год журнала: 2024, Номер 124(20), С. 11435 - 11522

Опубликована: Окт. 9, 2024

Arynes hold significance for the efficient fusion of (hetero) arenes with diverse substrates, advancing construction complex molecular frameworks. Employing multiple equivalents arynes is particularly effective in rapid formation polycyclic cores found optoelectronic materials and bioactive compounds. However, inherent reactivity often leads to side reactions, yielding unanticipated products underlining importance a detailed investigation into use fine-tune their reactivity. This review centers on methodologies syntheses organic reactions involving arynes, categorizing based mechanisms like cycloadditions, σ-bond insertions, nucleophilic additions, ene discusses aryne polymerization. The categorization these includes two primary approaches: first entails engagement within single step while second approach involves using equivalent sequentially across steps, both requiring strict control ensure precise participation each respective step. Additionally, provides an in-depth analysis selection precursors, organized chronologically by activation strategy, offering comprehensive background that supports main theme utilization. expectation remains this will be invaluable designing advanced engaging arynes.

Язык: Английский

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2:1 Adducts Arising from Reactions between Benzynes and 1,3,4-Oxadiazoles

Organic Letters, Год журнала: 2024, Номер 26(18), С. 3834 - 3839

Опубликована: Апрель 30, 2024

2:1 adducts arise from the reaction of 2,5-diaryl-1,3,4-oxadiazoles and benzynes generated hexadehydro-Diels-Alder (HDDA) reaction. Density functional theory computations support a mechanistic manifold that includes concerted S

Язык: Английский

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Switchable Synthesis of Tritylone Alcohols and 2-Benzoylbenzoate Esters from Spiroindane-1,3-diones

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(17), С. 12360 - 12369

Опубликована: Авг. 12, 2024

A solvent-controlled regioselective rearrangement reaction of spiroindane-1,3-diones with a leaving group has been developed. In acetonitrile solvent, the 3 were rearranged to provide tritylone alcohols, while 2-benzoylbenzoate ester derivatives obtained if reactions performed in alcohols.

Язык: Английский

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Construction of Naphtho[2,1-d]oxazoles and 1,4-Epoxyisoquinolines via Regioselectivity-Switchable Diels–Alder Reaction of 4-Alkenyloxazoles with Arynes

The Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 13, 2024

A Regioselectivity-switchable Diels-Alder reaction of arynes and 4-alkenyloxazoles was explored. By regulating the temperature polarity solvent, activity aryne controlled to selectively react with different favorable sites 4-alkenyloxazoles, providing naphtho[2,1-

Язык: Английский

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Five-membered ring systems with O and N atoms

Progress in heterocyclic chemistry, Год журнала: 2023, Номер unknown, С. 351 - 382

Опубликована: Янв. 1, 2023

Язык: Английский

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