Crystal structure of 3-(tert-butyldiphenylsilyl)-1-(2,6-dichlorophenyl)-2,2-diphenylpropan-1-ol, C37H36Cl2OSi DOI Creative Commons

Shuliang Zhang,

Zhao‐Zhao Zhou, Xi Chen

et al.

Zeitschrift für Kristallographie - New Crystal Structures, Journal Year: 2023, Volume and Issue: 239(1), P. 85 - 87

Published: Dec. 12, 2023

Abstract C 37 H 36 Cl 2 OSi, monoclinic P 1 / n (no. 14), a = 10.4363(14) Å, b 17.128(2) c 17.875(3) β 90.934(2)°, V 3194.8(8) Å 3 , Z 4, R gt ( F ) 0.0491, wR ref 0.1449, T 296.15 K.

Language: Английский

Recent advances in three-component radical acylative difunctionalization of unsaturated carbon–carbon bonds DOI
Jiaqiong Sun, Lihong V. Wang, Guangfan Zheng

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(18), P. 4488 - 4515

Published: Jan. 1, 2023

This review highlights the recent advances in radical acylated difunctionalization of unsaturated carbon–carbon bonds and focuses on mechanistic insights these transformations.

Language: Английский

Citations

31
General Method for Selective Three-Component Carboacylation of Alkenes via Visible-Light Dual Photoredox/Nickel Catalysis DOI
Zi-Kai Wang, Yaping Wang,

Zhi-Wu Rao

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(10), P. 1673 - 1677

Published: March 7, 2023

A photoredox/nickel dual catalytic protocol for the regioselective three-component carboacylation of alkenes with tertiary and secondary alkyltrifluoroborates as well acyl chlorides is described. This redox-neutral can be applied to rapid synthesis ketones high diversity complexity via a radical relay process. Many functional groups, allowing various commercially available chlorides, alkyltrifluoroborates, alkenes, are tolerated under these mild conditions.

Language: Английский

Citations

18
Visible-Light Photoredox-Catalyzed Divergent 1,2-Diacylation and Hydroacylation of Alkenes with Carboxylic Acid Anhydride DOI

Youkang Zhou,

Lirong Zhao,

Mingyou Hu

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(28), P. 5268 - 5272

Published: July 6, 2023

A photoredox-catalyzed divergent 1,2-dicarbonylation and hydroacylation of alkenes with acid anhydride is presented. This approach offers a mild efficient entry to 1,4-dicarbonyl compounds bearing all-carbon quaternary centers, exhibiting broad substrate scope high functional group compatibility. Hydrocarbonylaltion can also be realized by simply introducing proton source the reaction system. Mechanism investigations support radical addition/radical-polar crossover cascade.

Language: Английский

Citations

16
Visible-Light-Promoted Intermolecular β-Acyl Difunctionalization of Alkenes via Oxidative Radical-Polar Crossover DOI

Hao‐Cong Li,

Ke-Yuan Zhao,

Yan Tan

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(45), P. 8067 - 8071

Published: Nov. 8, 2023

A visible-light-induced β-acyl difunctionalization of alkenes with acyl oxime esters and various nucleophiles was developed to achieve molecular complexity from readily available raw materials via oxidative radical-polar crossover. variety nucleophiles, including NH-sulfoximines, indoles, indazole, trimethoxybenzene, were all effectively applicable the sustainable reaction system. The novel synthetic strategy features mild conditions, a broad substrate scope (39 examples), easy scale-up, excellent regioselectivity.

Language: Английский

Citations

13
Photochemical radical decarboxylative disulfuration of α-keto acids and oxamic acids DOI
Huangbin Sun,

Xueting Bin,

Qianfang Zhang

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(62), P. 8107 - 8110

Published: Jan. 1, 2024

A visible-light-induced directed decarboxylative disulfuration of α-keto acids and oxamic was developed. As a result, series versatile mono acyl disulfide derivatives synthesized under mild sustainable reaction conditions. This protocol has broad substrate scope, good functional-group tolerance, excellent synthetic applications.

Language: Английский

Citations

5
Nickel/Photo-Cocatalyzed Three-Component Alkyl-Acylation of Aryl-Activated Alkenes DOI
Pei Fan, Zhe Chen, Chuan Wang

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(49), P. 8877 - 8882

Published: Dec. 4, 2023

Herein, we disclose a nickel/photo-cocatalyzed three-component alkyl-acylation of aryl-substituted alkenes with aldehydes and electron-withdrawing-group-activated alkyl bromides, providing straightforward access to various ketones under mild ligand-free conditions. The photocatalyst TBADT plays dual role in activating the acyl C-H bond via hydrogen atom transfer reducing C-Br bromides single-electron transfer. While terminal C-C is forged through polarity-matched radical-type addition, nickel likely involved acylation step.

Language: Английский

Citations

10
Nickel/Photoredox Dual-Catalyzed, Regioselective 1,2-Carboacylation of Alkenes via Synergistic Alkyl and Benzoyl Radical Coupling DOI

Xian‐Chen He,

Jie Gao, Yang Li

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: May 2, 2025

A regioselective 1,2-carboacylation protocol of alkenes via nickel/photoredox dual catalysis has been successfully developed under mild conditions. wide range alkyl bromides, α-oxocarboxylic acids, and styrenes proved to be compatible the optimized conditions, affording corresponding products in up 91% yields. Mechanistically, key success this approach is temporal orchestration radical generation: nickel-catalyzed halogen atom transfer (XAT) for bromides photoredox-driven decarboxylation acids.

Language: Английский

Citations

0
Synthesis of α‐Branched Enones via Chloroacylation of Terminal Alkenes DOI Creative Commons
Jungwon Kim, Sven Müller, Tobias Ritter

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(49)

Published: Oct. 3, 2023

Here, we show the conversion of unactivated alkenes into α-branched enones via regioselective chloroacylation with acyl chlorides. The method relies upon initial in situ generation chlorine radicals directly from chloride precursor under cooperative nickel/photoredox catalysis. Subsequent HCl elimination provides and α,β-unsaturated esters that are not accessible conventional acylation approaches provide other, linear constitutional isomer.

Language: Английский

Citations

7
α-Acylation of Olefins via Photocatalysis DOI Open Access

Hongyu Hou,

Yuanyuan Cheng, Bin Chen

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 43(3), P. 1012 - 1012

Published: Jan. 1, 2023

The cheap and readily available olefin substrates have received much attention for the synthesis of structurally rich high value-added ketones, aldehydes, carboxylic acids their derivatives via α-acylation.Multicomponent tandem α-acylation olefins achieves efficiency selectivity by N-heterocyclic carbene or transition metal catalysis, albeit with narrow reaction modes substrates.Rapid growth photocatalysis in organic transformation has introduced new methodologies to undergo broad substrate scope.The research progress prospect future development this active field is highlighted.

Language: Английский

Citations

6
Ketone Synthesis via Irradiation-Induced Generation of a Persistent Ketyl Radical from Acyl Azolium Salts DOI

Shihao Li,

Chenglong Zheng,

Sheng Wang

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(35), P. 6522 - 6527

Published: Aug. 29, 2023

A novel three-component α-acylated difunctionalization of alkenes strategy has been developed on the basis a direct hydrogen atom transfer (HAT) process photoinduced acyl azolium salts. With simple irradiation without catalyst, variety olefins can be directly converted into ketone derivatives, including 1,4-dione, β-silyl ketone, 1,5-dione, etc. Mechanistic investigations indicated that unique reactivity azonium triplet excited state is crucial to strategy's success.

Language: Английский

Citations

6