Fe(<scp>ii</scp>)-Catalyzed azidation of polybutadienes using the Zhdankin reagent

Jung, Haeji; Lim, Yeong‐Gweon

doi:10.1039/c9py01009b

Cited by 7 publications

(5 citation statements)

References 31 publications

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“…Fe(II)-catalyzed diazidation of phenyl-terminated polybutadienes (PtPBs) using Zhdankin reagent generated in situ from readily available iodosobenzoic acid and TMSN 3 was reported by Lim and Jung. 162 In 2017, Bao et al developed a general copper-catalyzed ligand-free procedure for the diazidation of alkenes, dienes, and allenes using TMSN 3 as an azido source under aqueous or organic conditions (Scheme 36a). 163 By using this protocol, the authors successfully diazidated a range of bioactive natural products (nootkatone and estrone-based compounds) and drugs (exemestane and simvastatin).…”

Section: Rearomatization Along With the Extrusion Of Somentioning

confidence: 99%

“…The kinetic study supported the proposed mechanism, which involves a rate-determining 1,4-addition of TMSN 3 to chiral Lewis acid-activated α,β-unsaturated ketones followed by rapid electrophilic bromine capture of an enolate intermediate in the presence of BsNMeBr. 193 By using this catalytic system the chloro-and iodoazidation products (162,163) could also be obtained in good yields by using p-NsNCl 2 and NIS as the electrophilic chloro and iodo sources, respectively (Scheme 42b). Later, the same group extended the reaction scope to α,β-unsaturated amides, and α,βunsaturated esters by using a chiral L-PiPr 2 −Fe(II) catalyst.…”

Section: Rearomatization Along With the Extrusion Of Somentioning

confidence: 99%

“…In the absence of a polar cosolvent, • CHCl 2 formation is enabled, leading to the formation of carboazidation products. Fe(II)-catalyzed diazidation of phenyl-terminated polybutadienes (PtPBs) using Zhdankin reagent generated in situ from readily available iodosobenzoic acid and TMSN 3 was reported by Lim and Jung …”

Section: Azidation Of C–c Multiple Bondsmentioning

confidence: 99%

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New Strategies for the Synthesis of Aliphatic Azides

2021

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Aliphatic azides are a versatile class of compounds found in a variety of biologically active pharmaceuticals. These compounds are also recognized as useful precursors for the synthesis of a range of nitrogen-based scaffolds of therapeutic drugs, biologically active compounds, and functional materials. In light of the growing importance of aliphatic azides in both chemical and biological sciences, a vast array of synthetic strategies for the preparation of structurally diverse aliphatic azides have been developed over the past decades. However, to date, this topic has not been the subject of a dedicated review. This review aims to provide a concise overview of modern synthetic strategies to access aliphatic azides that have emerged since 2010. The discussed azidation reactions include (a) azidation of C–C multiple bonds, (b) azidation of C–H bonds, (c) the direct transformation of vinyl azides into other aliphatic azides, and (d) miscellaneous reactions to access aliphatic azides. We critically discuss the synthetic outcomes and the generality and uniqueness of the different mechanistic rationale of each of the selected reactions. The challenges and potential opportunities of the topic are outlined.

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Section: Rearomatization Along With the Extrusion Of Somentioning

confidence: 99%

Section: Rearomatization Along With the Extrusion Of Somentioning

confidence: 99%

Section: Azidation Of C–c Multiple Bondsmentioning

confidence: 99%

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New Strategies for the Synthesis of Aliphatic Azides

2021

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“…Phenyl‐terminated polybutadienes can be efficiently azidated by IBA in combination with TMSN 3 under iron catalysis conditions [53] . The authors reported easily controlled azidation rates by adjusting the amount of reagents, thereby final polymers with 5 %, 10 % and 15 % azide contents were obtained and characterized.…”

Section: Azidation Using In Situ Generated Azidoiodinanesmentioning

confidence: 99%

Hypervalent Iodine‐Mediated Azidation Reactions

et al. 2022

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Organic azides have found wide application in various fields of science and technology. This review summarizes recently developed approaches to the direct, one‐step synthesis of diverse organic azides utilizing hypervalent iodine reagents. The first part of review deals with the azidation using unstable azidoiodinanes generated in situ from common hypervalent iodine reagents (such as diacetoxyiodobenzene or iodosylbenzene) and a source of azide anion (TMSN3 or NaN3). The second part of review is dedicated to the application of stable azidobenziodoxoles as useful azidating reagents that allow selective direct azidation of C−H bonds or double carbon‐carbon bonds under mild reaction conditions. The use of azidobenziodoxoles eliminates the main disadvantages of the traditional approaches to organic azides, such as the need in pre‐functionalization of organic substrates and harsh reaction conditions. Synthetic application of azidobenziodoxoles made possible direct selective azidation of a plethora of organic substrates including complex molecules at the late synthetic stage.

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“…61 Iron catalysis was also used by Jung and Lim to azidate polymers. 62 The G. Liu group reported a palladium-catalyzed azidocarbonylation of alkenes proceeding via an iodonium bridge. 63 Cong et al used a ruthenium-catalyzed azidation of styrenes followed by a silver-catalyzed trifluoromethoxylation of the resulting radical.…”

Section: Short Review Synthesismentioning

confidence: 99%

Azidation with Hypervalent Iodine Reagents

Simonet‐Davin

Waser

2022

Synthesis

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In this short review, we describe applications of hypervalent iodine reagents for the azidation of organic compounds from the seminal publications to the most recent reports. After reviewing selected examples of azidations based on the use of in situ formed unstable non-cyclic reagents, we focus more in details on stable cyclic hypervalent iodine reagents. Important advances in the azidation of C–H bonds, alkenes as well as other transformations are described. Rather than being comprehensive, we selected to highlight the key reports that especially contributed to the advancement of research in the field in our opinion. Table of content: 1. Introduction 2. Non-Cyclic λ3-Iodanes 3. Heterocyclic λ3-Iodanes 3.1 Azidation of aliphatic C–H Bonds 3.2 Azidation of Alkenes 3.3 Other Azidations 4. Conclusion and Outlook

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Fe(ii)-Catalyzed azidation of polybutadienes using the Zhdankin reagent

Abstract: Phenyl-terminated polybutadienes (PtPBs) are efficiently converted to azidated PtPBs using the Zhdankin reagent generated in situ from iodosobenzoic acid and TMSN3 with an iron catalyst.

Cited by 7 publications

References 31 publications

New Strategies for the Synthesis of Aliphatic Azides

New Strategies for the Synthesis of Aliphatic Azides

Hypervalent Iodine‐Mediated Azidation Reactions

Azidation with Hypervalent Iodine Reagents

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