Enantiomer-selective Living Polymerization of rac-Phenyl Isocyanide Using Chiral Palladium Catalyst

Huang, Jian; Shen, Ling; Zou, Hui; Liu, Na

doi:10.1007/s10118-018-2136-5

Cited by 9 publications

(4 citation statements)

References 48 publications

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“…expectation that BPI/Pd polymer can form a helical CP by attachment of chiral substituent groups on iminonitrogens (Huang et al, 2018;Wang et al, 2019;Zhou et al, 2020).…”

Section: Chirality Induction In Bpi-3/pd Polymermentioning

confidence: 99%

A Chiral Metal-Organic 1D-Coordination Polymer Upon Complexation of Phenylene-Bridged Bipyrrole and Palladium (II) Ion

Nishinaka

Han

et al. 2020

Front. Chem.

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Metal-organic 1D-coordination polymers, having unique electronic and optical properties, are expected to be a novel advanced functional material capable of fabricating smart plastics, films, and fibers. In this study, we have synthesized a novel metal-organic 1D-coordination polymer composed of a phenylene-bridged bipyrrole bearing N-alkylimino groups (BPI) and palladium(II) ion. The BPI and Pd(II) form square planar bis(bidentate) complex to form a metal coordinated π-conjugation polymer (Poly-BPI/Pd). It is stable in solutions at room temperature, and allowed measurement of its average molecular weight in SEC (Mw = 106,000 and Mn = 18,000, Mw/Mn = 5.88). It also provided a reversible multi redox profile in cyclic voltammetry, most likely originating from strong π-electronic interactions between the BPI components via Pd ion. A variety of substituent groups can be attached to the imino-nitrogens of BPI. A coordination polymer composed of a BPI derivative bearing chiral alkyl chains and Pd(II) showed strong circular dichroism (CD) in the solution due to the unidirectional chiral conformation of the BPI components in the polymer backbone.

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“…expectation that BPI/Pd polymer can form a helical CP by attachment of chiral substituent groups on iminonitrogens (Huang et al, 2018;Wang et al, 2019;Zhou et al, 2020).…”

Section: Chirality Induction In Bpi-3/pd Polymermentioning

confidence: 99%

A Chiral Metal-Organic 1D-Coordination Polymer Upon Complexation of Phenylene-Bridged Bipyrrole and Palladium (II) Ion

Nishinaka

Han

et al. 2020

Front. Chem.

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“…Liu reported the enantiomer-selective polymerization of racemic isocyanides with chiral initiating system to produce optically active helical polymers. 59 In this study, a series of chiral palladium catalysts bearing chiral sulfinamide bisphosphine ligand was prepared to initiate the phenyl isocyanide derivative that contains L-, D-or rac-alanine residues with a long alkyl chain as the pendants through an amide linkage in highly enantiomer-selective manner. One of the enantiomers is preferentially polymerized through the kinetic resolution of a racemic monomer in the enantiomer-selective polymerization of racemic isocyanides.…”

Section: Enantiomer-selective Polymerizationmentioning

confidence: 99%

Selective synthesis of helical polymers

Wang

Liu

Gao

et al. 2022

Journal of Polymer Science

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Many researches have been done on synthetic helical polymers because of their wide applications such as chiral recognition, enantiomeric separation, asymmetric catalysis, circularly polarized luminescence, liquid crystallization and so on. Synthetic helical polymers can be generally divided into static helical polymers and dynamic helical polymers on the basis of whether the helix inversion barriers are high or low. And this mini review mainly describes the three common selectively synthetic methods of static helical polymers such as polymerization with chiral monomers, helix‐sense‐selective polymerization and enantiomer‐selective polymerization. We hope that this mini review can provide more ideas on synthesis of chiral materials and encourage further development on novel synthetic methods of helical polymers.

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“…Nickel-catalyzed polymerization of isocyanides to helical polyimines is extensively reported in literature [11,12]. Recently, significant advances have been made in using palladium catalysis for similar transformations to polyimines [13][14][15][16][17][18]. Due to the nature of this transformation, affording polymeric structures rather than small molecules, these examples will not be treated in this review.…”

Section: Isocyanidesmentioning

confidence: 99%

Recent Advances in Palladium-Catalyzed Isocyanide Insertions

et al. 2020

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Isocyanides have long been known as versatile chemical reagents in organic synthesis. Their ambivalent nature also allows them to function as a CO-substitute in palladium-catalyzed cross couplings. Over the past decades, isocyanides have emerged as practical and versatile C1 building blocks, whose inherent N-substitution allows for the rapid incorporation of nitrogeneous fragments in a wide variety of products. Recent developments in palladium catalyzed isocyanide insertion reactions have significantly expanded the scope and applicability of these imidoylative cross-couplings. This review highlights the advances made in this field over the past eight years.

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Enantiomer-selective Living Polymerization of rac-Phenyl Isocyanide Using Chiral Palladium Catalyst

Cited by 9 publications

References 48 publications

A Chiral Metal-Organic 1D-Coordination Polymer Upon Complexation of Phenylene-Bridged Bipyrrole and Palladium (II) Ion

A Chiral Metal-Organic 1D-Coordination Polymer Upon Complexation of Phenylene-Bridged Bipyrrole and Palladium (II) Ion

Selective synthesis of helical polymers

Recent Advances in Palladium-Catalyzed Isocyanide Insertions

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