Divergent Photosensitizer Controlled Reactions of 4‐Hydroxycoumarins and Unactivated Olefins: Hydroarylation and Subsequent [2+2] Cycloaddition DOI

Rui Chang,

Yubing Pang,

Juntao Ye

et al.

Angewandte Chemie, Journal Year: 2023, Volume and Issue: 135(45)

Published: Sept. 26, 2023

Abstract Herein, we report a photoinduced approach for hydroarylation of unactivated olefins using 4‐hydroxycoumarins as the arylating reagent. Key to success this reaction is conversion nucleophilic into electrophilic carbon radicals via photocatalytic arene oxidation, which not only circumvents polarity‐mismatch issue encountered under ionic conditions but also accommodates broad substrate scope and inhibits side reactions that were previously observed. Moreover, divergent reactivity was achieved by changing photocatalyst, enabling subsequent [2+2] cycloaddition deliver cyclobutane‐fused pentacyclic products are otherwise challenging access in high yields with diastereoselectivity. Mechanistic studies have elucidated mechanism origin reactivity.

Language: Английский

Divergent Photosensitizer Controlled Reactions of 4‐Hydroxycoumarins and Unactivated Olefins: Hydroarylation and Subsequent [2+2] Cycloaddition DOI Open Access

Rui Chang,

Yubing Pang,

Juntao Ye

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(45)

Published: Sept. 26, 2023

Herein, we report a photoinduced approach for hydroarylation of unactivated olefins using 4-hydroxycoumarins as the arylating reagent. Key to success this reaction is conversion nucleophilic into electrophilic carbon radicals via photocatalytic arene oxidation, which not only circumvents polarity-mismatch issue encountered under ionic conditions but also accommodates broad substrate scope and inhibits side reactions that were previously observed. Moreover, divergent reactivity was achieved by changing photocatalyst, enabling subsequent [2+2] cycloaddition deliver cyclobutane-fused pentacyclic products are otherwise challenging access in high yields with diastereoselectivity. Mechanistic studies have elucidated mechanism origin reactivity.

Language: Английский

Citations

11
Photobleachable coumarin-thioester derivatives with low cytotoxicity as visible-light photoinitiators for free radical and cationic photopolymerization DOI

Xuechun Li,

Jia Wei, Yanjing Gao

et al.

Progress in Organic Coatings, Journal Year: 2024, Volume and Issue: 191, P. 108404 - 108404

Published: April 3, 2024

Language: Английский

Citations

3
Construction of HaloTag-based macromolecular probe for multiple logic gates and photoactivatable bioimaging DOI
Andong Shao, Runqi Li,

Yaxi Li

et al.

International Journal of Biological Macromolecules, Journal Year: 2024, Volume and Issue: 278, P. 135043 - 135043

Published: Aug. 24, 2024

Language: Английский

Citations

0
Visible-light-induced dehydrogenation of dihydroquinolinones via the combination of energy transfer and hydrogen atom transfers DOI
Feng Jin, Huayang Tang, Hao Guo

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 19, 2024

A visible-light-induced dehydrogenation of dihydroquinolinones was developed using photocatalyst thioxanthone (TX) and oxidant tert -butyl benzoperoxoate.

Language: Английский

Citations

0
Divergent Photosensitizer Controlled Reactions of 4‐Hydroxycoumarins and Unactivated Olefins: Hydroarylation and Subsequent [2+2] Cycloaddition DOI

Rui Chang,

Yubing Pang,

Juntao Ye

et al.

Angewandte Chemie, Journal Year: 2023, Volume and Issue: 135(45)

Published: Sept. 26, 2023

Abstract Herein, we report a photoinduced approach for hydroarylation of unactivated olefins using 4‐hydroxycoumarins as the arylating reagent. Key to success this reaction is conversion nucleophilic into electrophilic carbon radicals via photocatalytic arene oxidation, which not only circumvents polarity‐mismatch issue encountered under ionic conditions but also accommodates broad substrate scope and inhibits side reactions that were previously observed. Moreover, divergent reactivity was achieved by changing photocatalyst, enabling subsequent [2+2] cycloaddition deliver cyclobutane‐fused pentacyclic products are otherwise challenging access in high yields with diastereoselectivity. Mechanistic studies have elucidated mechanism origin reactivity.

Language: Английский

Citations

0