Ring-opening copolymerization of hydroxyproline-derived thiolactones and lipoic acid derivatives

Zhang, Yi; Lu, Hua

doi:10.1039/d3py00467h

Polym. Chem.

2023

DOI: 10.1039/d3py00467h

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Ring-opening copolymerization of hydroxyproline-derived thiolactones and lipoic acid derivatives

Yi Zhang

Hua Lu

Abstract: Ring-opening copolymerization is an important means to combine the properties of two or more monomers and fine tune the functions of polymers. The copolymerization of two different types of monomers...

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2024

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Cited by 4 publications

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Palladium‐Catalyzed Carbonylative Transformation for the Synthesis of Tetracyclic Indoline Thioesters

Li,

Zhao,

et al. 2024

Adv Synth Catal

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Palladium‐catalyzed thioesterifications of (aza)indole‐tethered aryl iodides, Mo(CO)6, and sulfonyl chlorides are reported. A series of C2 thioester‐group substituted indoline‐fused ring compounds are efficiently constructed using intramolecular Heck‐cyclization and carbonylation chemistry involving N‐(2‐iodobenzoyl)indole. The salient features of this three‐component cascade sequence include the use of solid Mo(CO)6 as the carbon monoxide source and good functional group tolerance.

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Palladium‐Catalyzed Carbonylative Transformation for the Synthesis of Tetracyclic Indoline Thioesters

Li,

Zhao,

et al. 2024

Adv Synth Catal

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Recyclable Polythioesters and Poly(thioester‐co‐peptoid)s via Ring‐Opening Cascade Polymerization of Amino Acid N‐Carboxyanhydrides

Wang,

Tian,

2024

Angewandte Chemie

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Polythioesters (PTEs) are emerging sustainable polymers for their degradability and recyclability. However, low polymerizability of monomers and extensive side reactions often hampered the polymerization process. Moreover, copolymers containing both thioester and other types of functional groups in the backbone are highly desirable but rarely accomplished owing to several synthetic challenges. Here, we report the ring‐opening cascade polymerization (ROCAP) of N‐(2‐(acetylthio)ethyl)‐glycine N‐carboxyanhydrides (TE‐NCA) to afford recyclable PTEs and unprecedented poly(thioester‐co‐peptoid)s (P(TE‐co‐PP)s) in a controlled manner. By developing appropriated carboxylic acid‐tertiary amine dual catalysts, intramolecular S‐to‐N acyl shift is coupled into the ROCAP process of TE‐NA to yield products with dispersity below 1.10, molecular weight (Mn) up to 84.5 kDa, and precisely controlled ratio of thioester to peptoids. Random copolymerization of sarcosine NCA (Sar‐NCA) and TE‐NCA gives thioester‐embedded polysarcosine with facile backbone degradation while maintaining the water solubility. This work represents a paradigm shift for the ROP of NCAs, enriches the realm of cascade polymerizations, and provides a powerful synthetic approach to functional PTEs and P(TE‐co‐PP)s that are otherwise difficult or impossible to make.

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Recyclable Polythioesters and Poly(thioester‐co‐peptoid)s via Ring‐Opening Cascade Polymerization of Amino Acid N‐Carboxyanhydrides

Wang,

Tian,

2024

Angew Chem Int Ed

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Ring-opening copolymerization of hydroxyproline-derived thiolactones and lipoic acid derivatives

Abstract: Ring-opening copolymerization is an important means to combine the properties of two or more monomers and fine tune the functions of polymers. The copolymerization of two different types of monomers...

Cited by 4 publications

References 50 publications

Palladium‐Catalyzed Carbonylative Transformation for the Synthesis of Tetracyclic Indoline Thioesters

Palladium‐Catalyzed Carbonylative Transformation for the Synthesis of Tetracyclic Indoline Thioesters

Recyclable Polythioesters and Poly(thioester‐co‐peptoid)s via Ring‐Opening Cascade Polymerization of Amino Acid N‐Carboxyanhydrides

Recyclable Polythioesters and Poly(thioester‐co‐peptoid)s via Ring‐Opening Cascade Polymerization of Amino Acid N‐Carboxyanhydrides

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