PEG‐4000‐promoted palladium‐catalyzed <i>N</i>‐allylation in water: aminonaphthalene as an example

Shih, Chun-Jen; Shue, Yi-Jen; Yang, Shyh-Chyun

doi:10.1002/aoc.2899

Cited by 3 publications

(1 citation statement)

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“…The exocyclic double bond in the 3-position of the 1,5,9-triazacyclododecane ring, which is important for activity, enables an alternate macrocyclization strategy involving double N -allylation, as shown in Scheme (method B). Tsuji–Trost − N -allylation is well-precedented, − and hydroxyl groups in erythromycin A and other macrolide antibiotics have been bridged with an isobutylene unit by palladium-catalyzed reaction with 3-methylene-1,3-propanediyl bis( t -butylcarbonate) in THF or toluene. − In addition, palladium-catalyzed C -allylation with similar dielectrophiles has been used in natural product total syntheses. , …”

Section: Introductionmentioning

confidence: 99%

Tsuji–Trost Cyclization of Disulfonamides: Synthesis of 12-Membered, 11-Membered, and Pyridine-Fused Macrocyclic Triamines

Ali

Anugu²,

Chawla

et al. 2019

ACS Omega

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Macrocyclic triamine disulfonamides can be synthesized by double Tsuji–Trost N-allylation reaction of open-chain disulfonamides with 2-alkylidene-1,3-propanediyl bis(carbonates). The previously used Atkins–Richman macrocyclization method generally gives lower yields and requires more tedious purification of the product. Solvent, palladium source, ligand, and concentration have all been varied to optimize the yields of two key 12-membered ring bioactive compounds, CADA and VGD020. The new approach tolerates a wide range of functional groups and gives highest yields for symmetrical compounds in which the acidities of the two sulfonamide groups are matched, although the yields of unsymmetrical compounds are still generally good. The method has also been extended to the synthesis of 11-membered rings, pyridine-fused macrocycles, and products bearing an ester or aryl substituent on the exocyclic double bond.

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Section: Introductionmentioning

confidence: 99%

Tsuji–Trost Cyclization of Disulfonamides: Synthesis of 12-Membered, 11-Membered, and Pyridine-Fused Macrocyclic Triamines

Ali

Anugu²,

Chawla

et al. 2019

ACS Omega

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ChemInform Abstract: PEG‐4000‐Promoted Palladium‐Catalyzed N‐Allylation in Water: Aminonaphthalene as an Example.

2013

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PEG-4000-Promoted Palladium-Catalyzed N-Allylation in Water: Aminonaphthalene as an Example. -Addition of polyethylene glycol 4000 provides a significant improvement of the recently published protocol for N-(mono)allylation of 1-aminonaphthalene. -(SHIH, C.-J.; SHUE, Y.-J.; YANG, S.-Y.; YANG*, S.-C.; Appl. Organomet. Chem. 26 (2012) 10, 550-555, http://dx.doi.org/10.1002/aoc.2899 ; Sch. Pharm., Kaohsiung Med. Coll., Kaohsiung 807, Taiwan; Eng.) -Y. Steudel 13-073

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The Emerging Role of Polyethylene Glycol-Water (PEG-H₂O) as the Benign Mixed Solvent System in Organic Synthesis

Divyavani,

Padmaja,

Narayana Reddy

2025

COS

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Polyethylene glycol (PEG) has become a popular solvent and green catalyst for a variety of chemical reactions. It is a stable and biodegradable polymeric catalyst used in organic synthesis because it may be recycled numerous times without significantly losing its catalytic activity. Recently, the use of PEG-H2O mixed solvent systems in organic synthesis has gained popularity. This article presents an overview of PEG-H2O solvent system-mediated organic reactions, with a main focus on the importance of the solvent system. The study also focuses on recent developments in the PEG-H2O solvent system-mediated synthesis of a number of heterocy-clic compounds. Important characteristics of these PEG-H2O solvent systems include high atom economies, gentle reaction conditions, faster reaction rates, readily isolated side products and high yields. Results from various reactions showed that the choice of proper ratio of PEG: H2O solvent system plays a key role in product yields.

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PEG‐4000‐promoted palladium‐catalyzed N‐allylation in water: aminonaphthalene as an example

Cited by 3 publications

References 39 publications

Tsuji–Trost Cyclization of Disulfonamides: Synthesis of 12-Membered, 11-Membered, and Pyridine-Fused Macrocyclic Triamines

Tsuji–Trost Cyclization of Disulfonamides: Synthesis of 12-Membered, 11-Membered, and Pyridine-Fused Macrocyclic Triamines

ChemInform Abstract: PEG‐4000‐Promoted Palladium‐Catalyzed N‐Allylation in Water: Aminonaphthalene as an Example.

The Emerging Role of Polyethylene Glycol-Water (PEG-H₂O) as the Benign Mixed Solvent System in Organic Synthesis

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PEG‐4000‐promoted palladium‐catalyzed N‐allylation in water: aminonaphthalene as an example

Cited by 3 publications

References 39 publications

Tsuji–Trost Cyclization of Disulfonamides: Synthesis of 12-Membered, 11-Membered, and Pyridine-Fused Macrocyclic Triamines

Tsuji–Trost Cyclization of Disulfonamides: Synthesis of 12-Membered, 11-Membered, and Pyridine-Fused Macrocyclic Triamines

ChemInform Abstract: PEG‐4000‐Promoted Palladium‐Catalyzed N‐Allylation in Water: Aminonaphthalene as an Example.

The Emerging Role of Polyethylene Glycol-Water (PEG-H2O) as the Benign Mixed Solvent System in Organic Synthesis

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The Emerging Role of Polyethylene Glycol-Water (PEG-H₂O) as the Benign Mixed Solvent System in Organic Synthesis