CoH-catalyzed asymmetric remote hydroalkylation of heterocyclic alkenes: a rapid approach to chiral five-membered S- and O-heterocycles

Zhao, Lingzi; Liu, Feipeng; Zhuang, Yan; Shen, Mengyang; Xue, Jing; Wang, Xuchao; Zhang, Yuting; Rong, Zi-Qiang

doi:10.1039/d4sc01149j

Cited by 3 publications

(1 citation statement)

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“…Transition metal-catalyzed hydrofunctionalization of unsaturated olefins has been rapidly developed in recent years. − It provides a direct and efficient method for the formation of C(sp 3 )–C(sp 3 ) with stereocenters by introducing hydrogen and functional groups on unsaturated double bonds, − which employs stable and abundant alkenes as pronucleophiles instead of the moisture- and air-sensitive organometallic reagents typically required in traditional cross-coupling. − Inspired by these achievements and considering the importance of enantioenriched 3-methylpyrrolidine derivatives, we wondered whether a direct enantioselective installation of a methyl group on readily available 3-pyrrolines through low-valent CoH catalysis can be achieved. As is well-known, methyl is the smallest alkyl substituent.…”

Section: Introductionmentioning

confidence: 99%

Regio- and Enantioselective Hydromethylation of 3-Pyrrolines and Glycals Enabled by Cobalt Catalysis

Shen,

Niu,

Wang

et al. 2024

JACS Au

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Section: Introductionmentioning

confidence: 99%

Regio- and Enantioselective Hydromethylation of 3-Pyrrolines and Glycals Enabled by Cobalt Catalysis

Shen,

Niu,

Wang

et al. 2024

JACS Au

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Cobalt‐Catalyzed Hydroarylation of 2,3‐Dihydrofuran to Access α‐Arylated Tetrahydrofurans

Sun,

Lu,

2024

ChemCatChem

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α‐Arylated tetrahydrofurans, commonly found in biologically active molecules, exhibit diverse biologically activities and pharmacological effects. The functionalization of 2,3‐dihydrofuran offers a potential route for the synthesis of substituted tetrahydrofurans. Nevertheless, the development of earth‐abundant metal‐catalyzed regioselective hydrofunctionalization of 2,3‐dihydrofuran for the synthesis of substituted tetrahydrofurans remains to be pursued. Herein, we report a cobalt‐catalyzed hydroarylation of 2,3‐dihydrofuran, which serves as the first example of cobalt‐hydride‐catalyzed alkene hydroarylation. This reaction provides an efficient method for the synthesis of α‐arylated tetrahydrofurans with high reaction efficiency, exclusive α‐arylation selectivity, and remarkable functional group compatibility.

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Multifunctional Photobleaching Visible Radical/Cationic Photoinitiators Based on 5-Membered Aromatic Heterocyclic-Bis-Chalcone-Oxime Esters

Wu,

Gong,

Hou

et al. 2024

ACS Appl. Polym. Mater.

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Three photobleachable photoinitiators (PIs) with bischalcone-based oxime esters (PBAs) are designed and synthesized, including the electron donor (D) of a 5-membered aromatic heterocyclic (furan, thiophene, and pyrrole), electron acceptors (A) of cyclopentanone carbonyl, and oxime acrylate for visible photopolymerization. The mechanism for the generation of oxygen alkyl radicals, 5-membered aromatic heterocyclic radicals, and vinyl radicals demonstrates that PBAs are characterized by type I and type II PIs. Real-time Fourier-transform infrared (FT-IR) spectroscopy indicates that PBAs, effective onecomponent PIs, are able to rapidly initiate the photopolymerization of the double-bonded monomer when exposed to LED@385∼455 nm. In particular, PBA3 with pyrrole as D exhibits the highest double-bond conversion efficiency and photobleaching characteristics, and its acetonitrile solution completely fades within 8 min under LED@455 nm exposure. Moreover, the colorless bulk acrylate materials with thicknesses of up to 40 mm are produced through photopolymerization initiated by PBA3. Furthermore, PBA3/Iod as a twocomponent PI efficiently initiates hybrid photopolymerization of the double-bonded monomer and epoxy monomer to form an interpenetrating polymer network. Notably, PBA3 exhibits only a 1.9% migration ratio from polymerization films under illumination (60 min). Consequently, the research results provide an innovative avenue for the structural optimization of photobleaching PIs and extend their applicability to the field of deep photocuring.

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CoH-catalyzed asymmetric remote hydroalkylation of heterocyclic alkenes: a rapid approach to chiral five-membered S- and O-heterocycles

Abstract: Saturated heterocycles, which incorporate S and O heteroatoms, serve as fundamental frameworks in a diverse array of natural products, bioactive compounds, and pharmaceuticals. Herein, we describe a unique cobalt-catalyzed approach...

Cited by 3 publications

References 149 publications

Regio- and Enantioselective Hydromethylation of 3-Pyrrolines and Glycals Enabled by Cobalt Catalysis

Regio- and Enantioselective Hydromethylation of 3-Pyrrolines and Glycals Enabled by Cobalt Catalysis

Cobalt‐Catalyzed Hydroarylation of 2,3‐Dihydrofuran to Access α‐Arylated Tetrahydrofurans

Multifunctional Photobleaching Visible Radical/Cationic Photoinitiators Based on 5-Membered Aromatic Heterocyclic-Bis-Chalcone-Oxime Esters

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