One pot rhodium catalyzed, base and solvent-free synthesis of 2-(bromomethyl)furan derivatives and synthesis of Hashmi phenol through platinum catalyzed cascade cyclization

Sivaraman, Mahalingam; Muralidharan, D.; Perumal, Paramasivan T.

doi:10.1016/j.tetlet.2012.12.108

Cited by 5 publications

(1 citation statement)

References 34 publications

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“…Dimedone-derived iodonium ylides have been used in numerous synthetic transformations leading to various heterocyclic compounds. ,− For example, the fused dihydrofuran derivatives 495 can be obtained from iodonium ylide 493 and alkenes 494 under photochemical activation in high yields (Scheme ). The reaction using iodonium ylide 493 generated in situ from DIB and 1,3-cyclohexanedione under photochemical conditions gave products 495 in similar yields.…”

Section: Synthetic Applications Of Trivalent Iodine Compoundsmentioning

confidence: 99%

Advances in Synthetic Applications of Hypervalent Iodine Compounds

2016

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The preparation, structure, and chemistry of hypervalent iodine compounds are reviewed with emphasis on their synthetic application. Compounds of iodine possess reactivity similar to that of transition metals, but have the advantage of environmental sustainability and efficient utilization of natural resources. These compounds are widely used in organic synthesis as selective oxidants and environmentally friendly reagents. Synthetic uses of hypervalent iodine reagents in halogenation reactions, various oxidations, rearrangements, aminations, C−C bond-forming reactions, and transition metal-catalyzed reactions are summarized and discussed. Recent discovery of hypervalent catalytic systems and recyclable reagents, and the development of new enantioselective reactions using chiral hypervalent iodine compounds represent a particularly important achievement in the field of hypervalent iodine chemistry. One of the goals of this Review is to attract the attention of the scientific community as to the benefits of using hypervalent iodine compounds as an environmentally sustainable alternative to heavy metals.

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Section: Synthetic Applications Of Trivalent Iodine Compoundsmentioning

confidence: 99%

Advances in Synthetic Applications of Hypervalent Iodine Compounds

2016

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ChemInform Abstract: One‐Pot Rhodium‐Catalyzed, Base‐ and Solvent‐Free Synthesis of 2‐(Bromomethyl)furan Derivatives and Synthesis of Hashmi Phenol Through Platinum‐Catalyzed Cascade Cyclization.

2013

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One-Pot Rhodium-Catalyzed, Base-and Solvent-Free Synthesis of 2-(Bromomethyl)furan Derivatives and Synthesis of Hashmi Phenol Through Platinum--Catalyzed Cascade Cyclization. -Dicarbonyl iodonium ylides, generated in situ, react with propargyl bromide to produce furan derivatives (III). To demonstrate the synthetic utility, (IIIa) is converted into title compound (V). -(SIVARAMAN, M.; MURALIDHARAN, D.; PERUMAL*, P. T.; Tetrahedron Lett. 54 (2013) 12, 1507-1509, http://dx.

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