Photosensitized [2 + 2]-Cycloadditions of Dioxaborole: Reactivity Enabled by Boron Ring Constraint Strategy

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(46), P. 25061 - 25067

Published: Nov. 8, 2023

A strategy to achieve photosensitized [2 + 2] cycloadditions by means of temporary ring constraint is reported. Specifically, a dioxaborole prepared that undergoes with wide variety alkenes. This overcomes some challenges the cycloaddition acyclic substrates. The products can be easily transformed into cyclobutyl diols or 1,4-dicarbonyl compounds; latter represents formal alkene vicinal diacylation. synthetic utility this method shown in synthesis valuable heterocycles and biatriosporin D.

Language: Английский

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Photomediated Hydro(deutero)acylation of Olefins by Decarboxylative Addition of α-Oxocarboxylic Acids

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(4), P. 2741 - 2747

Published: Feb. 1, 2024

Acyl radicals have been generated from the decarboxylation of α-oxocarboxylic acids by using a readily accessible organic pyrimidopteridine photoredox catalyst under ultraviolet-A (UV-A) light irradiation. These reactive acyl were smoothly added to olefins such as styrenes and diverse Michael acceptors, with assistance H2O/D2O hydrogen donors, enabling easy access range ketones/β-deuterio ketones. A wide are compatible this reaction, which shows reliable, atom-economical, eco-friendly protocol. Furthermore, postsynthetic diversifications applications presented.

Language: Английский

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Photoredox-Neutral Deoxygenative Carboxylation of Acylated Alcohols with Tetrabutylammonium Oxalate

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(16), P. 11967 - 11973

Published: July 26, 2024

Herein, a photoredox-neutral strategy for carboxylation of acylated alcohols via C(sp3)–O bond activation and cleavage with tetrabutylammonium oxalate (TBAO) as the carbonyl source reductant well promoter is described. Neither pre-established CO2 atmosphere nor external electron donors are required TBAO crucial transformation. Various primary, secondary, tertiary could be smoothly converted to corresponding aryl acetic acids, which core structures diverse pharmaceutical drugs.

Language: Английский

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1,3-Difunctionalization of Alkenes by Cobaloxime Photocatalysis

Organic Letters, Journal Year: 2024, Volume and Issue: 26(32), P. 6809 - 6813

Published: Aug. 5, 2024

Represented herein is the first 1,3-difunctionalization of alkenes via photocatalysis. A single cobaloxime used to carry out two catalytic cycles in which not only as a photocatalyst initiate reaction but also metal catalyst for β-H elimination process. Electron-deficient alkenes, electron-rich and unactivated could be directly converted 1,3-bisphosphorylated products, even unsymmetric with H

Language: Английский

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Modular reductive radical-polar crossover-based acyl migration reactions of N-vinylimides with alkyl, silyl, and acyl radicals

RSC Advances, Journal Year: 2025, Volume and Issue: 15(15), P. 11582 - 11586

Published: Jan. 1, 2025

Generation of α-amino ketones: photocatalytic radical addition/acyl migration cascade processes were reported on reactions enamides with dihydroquinazolinones or acyl oxime acetates.

Language: Английский

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