Advances in Radical Oxidative C—H Alkylation of <i>N</i>‐Heteroarenes

Zhang, Junrong; Xu, Lijin; Liao, Yulin; Deng, Jiyong; Tang, Ri‐Yuan

doi:10.1002/cjoc.201600784

Cited by 47 publications

(23 citation statements)

References 47 publications

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“…Due to development of the synthetic technique, more and more functional polymers were fabricated and then used as the stabilizer and initiator (or control agent) in the synthesis of functional polymeric nanoparticles via PISA, which aroused increasing attention in a broad range of applications. [23,[54][55][56][57][58][59][60][61][62][63][64] Certain PISA-generated nanoparticles displayed stimuli-responsive shape shifting, typically between spherical micelles, worms, and vesicles, and this subject has been detailed in a recent review. [21] The stimuliresponsive morphology transitions of the polymeric nanoparticles with functional shell-forming blocks are usually very slow (it usually needs hours, days, or even weeks to complete the morphological transitions) due to the poor polymer chain mobility in their assembled state.…”

Section: General Considerationmentioning

confidence: 99%

Polymerization‐Induced Self‐Assembly of Functionalized Block Copolymer Nanoparticles and Their Application in Drug Delivery

Zhang

Hong

Pan

2018

Macromol. Rapid Commun.

218

183

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Drug delivery systems (DDS) based on functionalized polymeric nanoparticles have attracted considerable attention. Although great advances have been reported in the past decades, the fabrication efficiency and reproducibility of polymeric nanoparticles are barely satisfactory due to the intrinsic limitations of the traditional self-assembly method, which severely prevent further applications of the intelligent DDS. In the last decade, a new self-assembly method, which is usually called polymerization-induced self-assembly (PISA), has become a powerful strategy for the fabrication of the polymeric nanoparticles with bespoke morphology. The PISA strategy efficiently simplifies the fabrication of polymeric nanoparticles (combination of the polymerization and self-assembly in one pot) and allows the fabrication of polymeric nanoparticles at a relatively high concentration (up to 50 wt%), making it realistic for large-scale production of polymeric nanoparticles. In this review, the developments of PISA-based polymeric nanoparticles for drug delivery are discussed.

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Section: General Considerationmentioning

confidence: 99%

Polymerization‐Induced Self‐Assembly of Functionalized Block Copolymer Nanoparticles and Their Application in Drug Delivery

Zhang

Hong

Pan

2018

Macromol. Rapid Commun.

218

183

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“…[8] However,and as an important note, the use of Lewis or Brønsted acid catalysis,w hich can be assimilated with the Friedel-Crafts alkylation and would, therefore,b eo utside the scope of this Review,w ill not be covered. [8] However,and as an important note, the use of Lewis or Brønsted acid catalysis,w hich can be assimilated with the Friedel-Crafts alkylation and would, therefore,b eo utside the scope of this Review,w ill not be covered.…”

Section: Introductionmentioning

confidence: 99%

“…Although this Review will mostly focus on metal-catalyzed reactions,s ome metal-free processes will also be included to make sure that major developments in the radical alkylation of C À Hbonds of arenes will be covered, since they also provide excellent processes for the alkylation of abroad range of heteroarenes. [8] However,and as an important note, the use of Lewis or Brønsted acid catalysis,w hich can be assimilated with the Friedel-Crafts alkylation and would, therefore,b eo utside the scope of this Review,w ill not be covered. [9] As in our previous review, [4] fort he sake of conciseness and clarity,o nly the most representative and significant examples of reactions for the introduction of specific alkyl groups such as benzyl, allyl, succinimides,o r hydroxyalkyl chains,w ill be discussed and intramolecular variants will not be covered.…”

Section: Introductionmentioning

confidence: 99%

Beyond Friedel and Crafts: Directed Alkylation of C−H Bonds in Arenes

2019

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The alkylation of arenes is one of the most fundamental transformations in chemical synthesis leading to privileged scaffolds in many areas of science. Classical methods for the introduction of alkyl groups to arenes are mostly based on the Friedel-Crafts reaction, radical additions, metallation or pre-functionalization of the arene: these methods however suffer from limitations in scope, efficiency and selectivity. Moreover, they are based on the innate reactivity of the starting arene, favoring the alkylation at a certain position and rendering the introduction of alkyl chains at other positions much more challenging. This can be addressed by the use of a directing group facilitating, in the presence of a metal catalyst, the regioselective alkylation of a C-H bond. These directed alkylations of C-H bonds in arenes are overviewed, in a comprehensive manner, in this review article.

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“…Although this Review will mostly focus on metal‐catalyzed reactions, some metal‐free processes will also be included to make sure that major developments in the radical alkylation of C−H bonds of arenes will be covered, since they also provide excellent processes for the alkylation of a broad range of heteroarenes . However, and as an important note, the use of Lewis or Brønsted acid catalysis, which can be assimilated with the Friedel–Crafts alkylation and would, therefore, be outside the scope of this Review, will not be covered .…”

Section: Introductionmentioning

confidence: 99%

Beyond Friedel and Crafts: Innate Alkylation of C−H Bonds in Arenes

Evano

Theunissen

2019

Angew Chem Int Ed

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Alkylated arenes are ubiquitous molecules and building blocks commonly utilized in most areas of science where there is a need for small organic molecules. Despite its apparent simplicity, the regioselective alkylation of arenes is still a challenging transformation in a lot of cases. Classical methods for the introduction of alkyl groups on arenes, which include the venerable Friedel-Crafts reaction, radical additions, metallation or pre-functionalization of the arene, as well as alternatives such as the directed alkylation of C-H bonds, still suffer from severe limitations in terms of scope, efficiency and selectivity. This can be addressed by exploiting the innate reactivity of some (hetero)arenes, in which electronic and steric properties, governed (or not) by the presence of one (or multiple) heteroatom(s) ensure high levels of regioselectivity. These innate alkylations of C-H bonds in (hetero)arenes will be overviewed, in a comprehensive manner, in this review article.

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Advances in Radical Oxidative C—H Alkylation of N‐Heteroarenes

Cited by 47 publications

References 47 publications

Polymerization‐Induced Self‐Assembly of Functionalized Block Copolymer Nanoparticles and Their Application in Drug Delivery

Polymerization‐Induced Self‐Assembly of Functionalized Block Copolymer Nanoparticles and Their Application in Drug Delivery

Beyond Friedel and Crafts: Directed Alkylation of C−H Bonds in Arenes

Beyond Friedel and Crafts: Innate Alkylation of C−H Bonds in Arenes

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