Visible Light-Mediated Aza-Norrish–Yang Type Cyclization

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 6473 - 6485

Published: April 6, 2025

Language: Английский

Microfluidic Photocatalytic Ring Expansion of Sulfonium Salts for the Synthesis of Cyclic Sulfides

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 6507 - 6513

Published: April 6, 2025

Cyclic sulfides are relevant building blocks in medicinal and synthetic chemistry, with applications ranging from drug discovery to materials science. However, the synthesis of medium-sized cyclic (6-8-membered rings) remains largely underdeveloped. Herein, we report a photocatalytic ring-expansion strategy for sulfonium salts, granting access six-, seven-, eight-membered very high regio- diastereocontrol. The implementation method under continuous flow was key increasing efficiency minimizing product decomposition. Mechanistic investigations revealed formation benzylic radicals carbocation intermediates that control diastereoselectivity observed. Finally, utility this approach demonstrated sulfoxides sulfones, which can be easily obtained corresponding sulfide products.

Language: Английский

Access to Methylidene-Azaspiro[4.5]decatrienones via Radical-Promoted Domino Thio-Functionalization/Dearomative Ipso-Annulation

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 9, 2025

An unprecedented approach involving radical-mediated sulfonylation/dearomative ipso-annulation of N-(methyl-2-phenylacetate)propiolamides using arylsulfonyl radical, generated from aryl diazonium salt in the presence DABSO, is developed. This strategy provides uniquely substituted 3-sulfonyl azaspiro[4.5]decatrienones good yields. The developed has also been extended fruitfully to 3-thiocyano aza-spirocycles through domino thiocyanation/dearomative ipso-annulation.

Language: Английский