Ligand-controlled cobalt-catalyzed isomerization and reductive C–O bond cleavage of allylic ethers DOI

Lijun Chang,

Cai Cheng, Ran Chen

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(18), P. 4643 - 4648

Published: Jan. 1, 2023

Cobalt-catalyzed isomerization and reductive cleavage of allylic ethers are described, which controlled by the selection ligand.

Language: Английский

1,3-diene-based AIEgens: Stereoselective synthesis and applications DOI Creative Commons

Xiao‐Mei Nong,

Ao Gu,

Shuyang Zhai

et al.

iScience, Journal Year: 2024, Volume and Issue: 27(3), P. 109223 - 109223

Published: Feb. 15, 2024

SummaryIn recent years, significant advancements have been made in the synthesis and application of 1,3-dienes. This specific structural motif has garnered attention from researchers materials science biology due to its unique aggregation-induced emission (AIE) properties extensive conjugation systems. The luminescent characteristics these compounds are notably influenced by geometry two double bonds. Therefore, it is essential consolidate stereoselective synthetic strategies for comprehensive review seeks elucidate diverse techniques employed attain stereo-control 1,3-diene-based AIE luminogens (AIEgens). Particular emphasis placed on comprehending determinants stereoselectivity exploring array substrates amenable methods. Furthermore, underscores exhibited their utility organic light-emitting diodes (OLEDs), stimuli-responsive materials, sensors, bioimaging, photodynamic therapy (PDT).Graphical abstract

Language: Английский

Citations

7
Regio‐ and Stereo‐Selective Isomerization of Borylated 1,3‐Dienes Enabled by Selective Energy Transfer Catalysis DOI Creative Commons

Byeongseok Kweon,

Lukas Blank,

Julia Soika

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(22)

Published: March 28, 2024

Abstract Configurationally‐defined dienes are pervasive across the bioactive natural product spectrum, where they typically manifest themselves as sorbic acid‐based fragments. These C 5 motifs reflect biosynthesis algorithms that facilitate their construction. To complement established biosynthetic paradigms, a chemical platform to construction of stereochemically defined, functionalizable by light‐enabled isomerization has been devised. Enabled selective energy transfer catalysis, variety substituted β‐boryl acid derivatives can be isomerized in regio‐ and stereo‐selective manner (up 97 : 3). Directionality is guided stabilizing n O →p B interaction product: this constitutes formal anti ‐hydroboration starting alkyne. This operationally simple reaction employs low catalyst loadings (1 mol %) complete 1 h. X‐ray analysis supports hypothesis leads chromophore bifurcation: provides structural foundation for transfer.

Language: Английский

Citations

5
Photoinduced Copper-Catalyzed 1,2-Difunctionalization of 1,3-Dienes with Aryl Diselenides DOI

Shengkun Guo,

Xiaoyu Shen, Xiaoyun Chen

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(22), P. 15969 - 15974

Published: Oct. 30, 2023

Described herein is a photoinduced copper-catalyzed 1,2-difunctionalization of 1,3-dienes. The selenium atom radical was generated by the visible light irradiation diselenides, triggering addition with 1,3-dienes to form allyl intermediate. Subsequent rapid Z/E isomerization allowed for thermodynamically favorable intermediate formation and enabled copper catalyzed stereoselective functionalization various nucleophiles.

Language: Английский

Citations

11
A palladium catalyzed stereo-convergent aminocarbonylation of 1,3-dienes with nitroarenes: synthesis of (E,E)-dienamides DOI

Jin‐Liang Lu,

Yun Chan Kang,

Zhi Zhang

et al.

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(23), P. 6505 - 6512

Published: Jan. 1, 2022

A palladium catalyzed stereo-convergent aminocarbonylation of 1,3-dienes with nitroarenes has been developed. The reaction mixtrues E / Z isomers reacted and produced ( , )-dienamides high stereoselectivities.

Language: Английский

Citations

15
Cobalt-Catalyzed Asymmetric Hydrosilylation of α-Oxygenated Ketones DOI

Huiting Wen,

Yifei Chen,

Lanxuan Shi

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(13), P. 2184 - 2189

Published: March 24, 2023

An asymmetric hydrosilylation of α-oxygenated ketones was developed under the catalysis Co(OAc)2 in combination with a chiral phosphine-amido-oxazoline (PAO) ligand, providing mild, efficient, and enantioselective access to variety synthetically useful 1,2-diol derivatives. This protocol can be carried out at gram scale catalyst loading 1 mol %, its synthetic utility demonstrated by efficient conversion optically enriched products into α-hydroxy acid, 1,3-dioxolan-2-one, ethylene oxide, 1,2,3-1H-triazole.

Language: Английский

Citations

6
Ligand-Controlled Cobalt-Catalyzed Regiodivergent and Stereoselective Ring-Opening Isomerization of Vinyl Cyclopropanes DOI

Wei Wang,

Qiao Li,

Man Xu

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(23), P. 5004 - 5009

Published: June 3, 2024

A ligand-controlled regiodivergent and stereoselective ring-opening isomerization of vinylcyclopropane was developed with cobalt catalysis. Employing the commercially available Xantphos ligand, reactions afforded exclusively linear-type 1,3-dienes as products. Interestingly, when switching ligand to an amido-diphosphine (PNP), branched-type were obtained high regioselectivity stereoselectivity. Preliminary mechanistic investigations suggested that a π-allyl metal metal-hydride species are involved key intermediates in two transformations, respectively.

Language: Английский

Citations

1
Nickel-Catalyzed Stereoconvergent C(sp2)–F Alkenylation of Monofluoroalkenes DOI
Xiaowei Li,

Wenlong Shan,

Nan Zhou

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(40), P. 8521 - 8526

Published: Sept. 27, 2024

The stereoconvergent synthesis of a single stereoisomer from

Language: Английский

Citations

1
Regio‐ and Stereo‐Selective Isomerization of Borylated 1,3‐Dienes Enabled by Selective Energy Transfer Catalysis DOI Creative Commons

Byeongseok Kweon,

Lukas Blank,

Julia Soika

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(22)

Published: March 28, 2024

Abstract Configurationally‐defined dienes are pervasive across the bioactive natural product spectrum, where they typically manifest themselves as sorbic acid‐based fragments. These C 5 motifs reflect biosynthesis algorithms that facilitate their construction. To complement established biosynthetic paradigms, a chemical platform to construction of stereochemically defined, functionalizable by light‐enabled isomerization has been devised. Enabled selective energy transfer catalysis, variety substituted β‐boryl acid derivatives can be isomerized in regio‐ and stereo‐selective manner (up 97 : 3). Directionality is guided stabilizing n O →p B interaction product: this constitutes formal anti ‐hydroboration starting alkyne. This operationally simple reaction employs low catalyst loadings (1 mol %) complete 1 h. X‐ray analysis supports hypothesis leads chromophore bifurcation: provides structural foundation for transfer.

Language: Английский

Citations

1
Ligand-controlled cobalt-catalyzed isomerization and reductive C–O bond cleavage of allylic ethers DOI

Lijun Chang,

Cai Cheng, Ran Chen

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(18), P. 4643 - 4648

Published: Jan. 1, 2023

Cobalt-catalyzed isomerization and reductive cleavage of allylic ethers are described, which controlled by the selection ligand.

Language: Английский

Citations

2