Organophotocatalyzed C‐Si Bond Fragmentation Using Silyl Ethers as Radical Precursors DOI Creative Commons
Adrián Luguera Ruiz,

Valentina Benazzi,

Federico Tucci

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(19), P. 4132 - 4138

Published: July 19, 2024

Abstract In this work, silyl ethers of phenols and alcohols have been successfully prepared tested as neutral carbon (silicon) centered radical precursors. The organophotocatalyzed oxidation (by the Fukuzumi catalyst) these caused cleavage a C−Si (or Si−Si) bond for release desired to be used forging C( sp 3 ) −C( −Si) bonds via Giese reaction.

Language: Английский

Organocatalyzed Hydroacylation of Enones by Photosensitization of Acyl Silanes DOI

Shiv Shankar Patel,

Samiksha Gupta,

Chandra Bhushan Tripathi

et al.

Chemistry - An Asian Journal, Journal Year: 2024, Volume and Issue: 19(11)

Published: April 11, 2024

A mild protocol for hydroacylation of enones through photosensitization acyl silanes with thioxanthone under blue light (455 nm) irradiation is reported. Brønsted acid used as a cocatalyst in the reaction. The versatility method demonstrated inter- and intramolecular product applied synthesizing an anti-HCV agent. Mechanistic insights are also provided control experiments.

Language: Английский

Citations

4
Acylsilanes as Weakly Coordinating Directing Groups for Metal-Catalyzed C–H Functionalization DOI
Rowan L. Pilkington, Daniel L. Priebbenow

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 6881 - 6894

Published: April 14, 2025

Language: Английский

Citations

0
Synthetic utility of functionalized alkylsilyl peroxides for Fe-catalyzed and visible-light-promoted radical transformation DOI Creative Commons
Jiahao Liu,

Shiyong Liu,

Zhe Wang

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(13), P. 4757 - 4762

Published: Jan. 1, 2024

α-Keto-, β-acetoxy- and β-amidoalkylsilyl peroxides are prepared from various precursors utilized for Fe-catalyzed visible-light-promoted radical functionalization with coupling partners under mild conditions a broad substrate scope.

Language: Английский

Citations

3
Acylsilanes in Transition-Metal-Catalyzed and Photochemical Reactions: Clarifying Product Formation DOI
Liselle Atkin,

Hannah J. Ross,

Daniel L. Priebbenow

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(19), P. 14205 - 14209

Published: Sept. 22, 2023

Acylsilanes are able to react as nucleophilic carbene precursors, electrophiles, and directing groups in C–H functionalization. To date, some of the products reportedly formed during transition-metal-catalyzed photochemical reactions involving acylsilanes have been incorrectly assigned. provide clarity, we herein address these structural misassignments detail revised structures. New insights into reactivity were also afforded via discovery that light-induced siloxy carbenes participate intramolecular 1,2-carbonyl addition proximal esters.

Language: Английский

Citations

7
Hydrogen‐Bonding Organocatalysis Enabled Photocatalytic Intramolecular [2+2]‐Cycloaddition Reaction DOI Creative Commons

Stefania Perulli,

Om Desai, Sandra Ardevines

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(4), P. 751 - 756

Published: Jan. 15, 2024

Abstract The combination of organocatalytic activation and photocatalysis for enabling the intramolecular [2+2]‐cycloaddition enone‐ene substrates bearing one Lewis base binding site is reported. While in a variety solvents poor conversion or no reaction takes place absence hydrogen bonding catalyst, corresponding ring‐fused cyclobutane products could be built moderate to good yields using synergistic dual iridium‐urea co‐catalytic system. Control mechanistic studies supported postulated interaction between organocatalyst substrate, which proved essential an efficient energy transfer from photosensitizer.

Language: Английский

Citations

1
Organophotocatalyzed C‐Si Bond Fragmentation Using Silyl Ethers as Radical Precursors DOI Creative Commons
Adrián Luguera Ruiz,

Valentina Benazzi,

Federico Tucci

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(19), P. 4132 - 4138

Published: July 19, 2024

Abstract In this work, silyl ethers of phenols and alcohols have been successfully prepared tested as neutral carbon (silicon) centered radical precursors. The organophotocatalyzed oxidation (by the Fukuzumi catalyst) these caused cleavage a C−Si (or Si−Si) bond for release desired to be used forging C( sp 3 ) −C( −Si) bonds via Giese reaction.

Language: Английский

Citations

0