Recent Advances in Visible Light‐induced Asymmetric Transformations of Carbonyl Compounds into Chiral Alcohols DOI
Liuzhen Hou, Xiaohua Liu, Weidi Cao

et al.

ChemCatChem, Journal Year: 2023, Volume and Issue: 15(21)

Published: Aug. 16, 2023

Abstract Visible light‐induced photocatalysis has been widely investigated, which offers exciting opportunities to build new catalytic platforms that are unattainable under ground state conditions. Asymmetric a longstanding challenge due the high reactivity of photogenerated intermediates leading strong background reaction. Carbonyl group is an important fundamental scaffold in organic synthesis. The photocatalytic asymmetric transformations carbonyl compounds for synthesizing enantioenriched secondary and tertiary alcohols significant value but remain problematic. Even so, series intriguing works concerning this topic have reported recent year. This review summarizes advances area, mainly dividing into single synergetic catalyst systems, mechanism each reaction discussed.

Language: Английский

Photoinduced generation of ketyl radicals and application in C–C coupling withoutexternal photocatalyst DOI
Y. Yan, Gang Li, Jiani Ma

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(10), P. 4129 - 4136

Published: Jan. 1, 2023

A green and efficient procedure for photoinduced generation of ketyl radicals with no use any external photocatalyst is demonstrated, enabling a series important C–C coupling reactions in synthetic chemistry.

Language: Английский

Citations

22

Sequential Modifications of Metal–Organic Layer Nodes for Highly Efficient Photocatalyzed Hydrogen Atom Transfer DOI
Haifeng Zheng, Yingjie Fan,

Abigail L. Blenko

et al.

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(18), P. 9994 - 10000

Published: May 1, 2023

Herein, we report the synthesis of a bifunctional photocatalyst, Zr-OTf-EY, through sequential modifications metal cluster nodes in metal-organic layer (MOL). With eosin Y and strong Lewis acids on nodes, Zr-OTf-EY catalyzes cross-coupling reactions between various C-H compounds electron-deficient alkenes or azodicarboxylate to afford C-C C-N coupling products, with turnover numbers up 1980. In Zr-OTf-EY-catalyzed reactions, acid sites bind increase their local concentrations electron deficiency for enhanced radical additions, while EY is stabilized by site isolation MOL long-lived catalyst hydrogen atom transfer. The proximity photostable enhances catalytic efficiency approximately 400 times over homogeneous counterpart reactions.

Language: Английский

Citations

21

Photoalkylation/-arylation of ortho-Diketones with Unactivated Organic Halides DOI

Xiao-Yu Wang,

Yongqin He, Yi Zhou

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(21), P. 3847 - 3852

Published: May 22, 2023

A new method for conducting a reductive alkylation/arylation of 1,2-diketones using visible light and unactivated organic halides is presented in this article. This technique does not require photocatalyst employs Et3N, tertiary amine, as promoter. amine aids generating ketyl radical an α-aminoalkyl radical, which engages C-X bond activation via halogen atom transfer process (XAT). approach's success hinges on utilizing Et3N the article's mild straightforward protocol allows significantly expanding halide substrates, including primary, secondary, aromatic various functional groups.

Language: Английский

Citations

19

Enantioselective Dearomatization of Indoles via SmI2-Mediated Intermolecular Reductive Coupling with Ketones DOI
Wenyun Zhang,

Hu-Chong Wang,

Ye Wang

et al.

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(18), P. 10314 - 10321

Published: April 26, 2023

Samarium diiodide (SmI2) mediated reductive coupling reactions are powerful methods for the construction of carbon-carbon bond in organic synthesis. Despite extensive development recent decades, successful examples corresponding asymmetric remained scarce, probably due to involvement highly reactive radical intermediates. In this Article, we report an enantioselective dearomatization indoles via SmI2-mediated intermolecular with ketones. The utilization samarium reductant supported by chiral tridentate aminodiol ligands allows facile synthesis indoline molecules bearing two contiguous stereogenic centers high yields (up 99%) and stereoselectivity 99:1 er >20:1 dr). Combined experimental computational investigations suggested that parallel single-electron transfer each substrate from radical-radical recombination manner, which is a unique mechanistic scenario reactions.

Language: Английский

Citations

17

Recent Advances in Visible Light‐induced Asymmetric Transformations of Carbonyl Compounds into Chiral Alcohols DOI
Liuzhen Hou, Xiaohua Liu, Weidi Cao

et al.

ChemCatChem, Journal Year: 2023, Volume and Issue: 15(21)

Published: Aug. 16, 2023

Abstract Visible light‐induced photocatalysis has been widely investigated, which offers exciting opportunities to build new catalytic platforms that are unattainable under ground state conditions. Asymmetric a longstanding challenge due the high reactivity of photogenerated intermediates leading strong background reaction. Carbonyl group is an important fundamental scaffold in organic synthesis. The photocatalytic asymmetric transformations carbonyl compounds for synthesizing enantioenriched secondary and tertiary alcohols significant value but remain problematic. Even so, series intriguing works concerning this topic have reported recent year. This review summarizes advances area, mainly dividing into single synergetic catalyst systems, mechanism each reaction discussed.

Language: Английский

Citations

17