Organic Dye Photocatalyzed Synthesis of Functionalized Lactones and Lactams via a Cyclization–Alkynylation Cascade DOI Creative Commons
Diana Cavalli, Jérôme Waser

Organic Letters, Год журнала: 2024, Номер 26(20), С. 4235 - 4239

Опубликована: Май 13, 2024

An organic dye photocatalyzed lactonization-alkynylation of easily accessible homoallylic cesium oxalates using ethynylbenziodoxolone (EBX) reagents has been developed. The reaction gave access to valuable functionalized lactones and lactams in up 88% yield via the formation two new C-C bonds. transformation was carried out on primary, secondary, tertiary alcohols primary amines could be applied synthesis spirocyclic compounds as well fused bridged bicyclic lactones.

Язык: Английский

Copper-Catalyzed/Hypervalent Iodine-Mediated Functionalization of Unactivated Compounds DOI Open Access
Marta Papis, Francesca Foschi, Sara Colombo

и другие.

Catalysts, Год журнала: 2023, Номер 13(9), С. 1243 - 1243

Опубликована: Авг. 26, 2023

The functionalization of unactivated substrates through the combination copper catalysts and hypervalent iodine reagents represents a versatile tool in organic synthesis to access various classes compounds. derivatives can be used simply as oxidizing agents regenerate catalytic species or they associate starting material. In this review, special attention will paid methodologies which provide introduction nucleophiles into reagent by use suitable benziodoxol(on)es iodonium salts. Many reactions concern C- N-arylations, but may also involve formation different carbon–carbon carbon–nitrogen bonds, carbon–oxygen well carbon–halogen carbon–phosphorus bonds.

Язык: Английский

Процитировано

6

One-pot synthesis of functionalized bis(trifluoromethylated)benziodoxoles from iodine(i) precursors DOI
Tobias M. Milzarek, Nieves P. Ramirez,

Xingyu Liu

и другие.

Chemical Communications, Год журнала: 2023, Номер 59(84), С. 12637 - 12640

Опубликована: Янв. 1, 2023

Bis(trifluoromethylated)benziodoxoles (Bx) are broadly used cyclic hypervalent iodine reagents due to their stability and unique chemical properties. However, current methods access them require several steps long reaction times, making synthesis tedious. Herein, a direct one-pot of bis(trifluoromethylated) Bx from iodine(I) precursors is reported, enabling the functionalized reagents.

Язык: Английский

Процитировано

6

SOMOphilic alkyne vs radical-polar crossover approaches: The full story of the azido-alkynylation of alkenes DOI Creative Commons
Julien Borrel, Jérôme Waser

Beilstein Journal of Organic Chemistry, Год журнала: 2024, Номер 20, С. 701 - 713

Опубликована: Апрель 3, 2024

We report the detailed background for discovery and development of synthesis homopropargylic azides by azido-alkynylation alkenes. Initially, a strategy involving SOMOphilic alkynes was adopted, but only resulted in 29% yield desired product. By switching to radical-polar crossover approach after optimization, high (72%) azide reached. Full insights are given about factors that were essential success optimization process.

Язык: Английский

Процитировано

2

PIDA-promoted metal-free [3 + 2] heteroannulation of β-ketothioamides with 4-hydroxy coumarins: chemo-/regioselective access to furo[3,2-c]chromen-4-ones at room temperature DOI

Anup Kumar Yadav,

Dhananjay Yadav,

Vipin Kumar

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(21), С. 4326 - 4331

Опубликована: Янв. 1, 2024

A viable protocol to access furo[3,2- c ]chromen-4-ones engaging 4-hydroxy coumarins and thioamides mediated by phenyliodine( iii ) diacetate at room temperature in a highly efficient manner is developed.

Язык: Английский

Процитировано

2

Organic Dye Photocatalyzed Synthesis of Functionalized Lactones and Lactams via a Cyclization–Alkynylation Cascade DOI Creative Commons
Diana Cavalli, Jérôme Waser

Organic Letters, Год журнала: 2024, Номер 26(20), С. 4235 - 4239

Опубликована: Май 13, 2024

An organic dye photocatalyzed lactonization-alkynylation of easily accessible homoallylic cesium oxalates using ethynylbenziodoxolone (EBX) reagents has been developed. The reaction gave access to valuable functionalized lactones and lactams in up 88% yield via the formation two new C-C bonds. transformation was carried out on primary, secondary, tertiary alcohols primary amines could be applied synthesis spirocyclic compounds as well fused bridged bicyclic lactones.

Язык: Английский

Процитировано

2