Hypervalent Iodine Chemistry: 25 Years of Development at the University of Thessaloniki

Varvoglis, Anastasios; Spyroudis, Spyros

doi:10.1055/s-1998-1619

Cited by 73 publications

(19 citation statements)

References 61 publications

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“…Continuing the exploration of the chemistry of hypervalent iodine reagents [5], we investigated the possibility of analogous cyclization reactions using enamino carbonyl systems of type I. Recently we reported the isolation of stable iodonium salts of type II, resulting from enamino carbonyl compounds such as amino quinones [6], aminocrotonates [7] and cyclic enaminones [8] (in the last case the Ph of the iodonium salt group had been replaced by the CF 3 CH 2 group).…”

Section: Resultsmentioning

confidence: 99%

Spiro Cyclohexadienones from the Reaction of Phenolic Enaminone Derivatives with Hypervalent Iodine Reagents

et al. 2000

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Section: Resultsmentioning

confidence: 99%

Spiro Cyclohexadienones from the Reaction of Phenolic Enaminone Derivatives with Hypervalent Iodine Reagents

et al. 2000

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“…4,23 4¢ was also prepared by reported procedures. [12][13][14] All the physical properties of 5 reported in this paper were from the reactions under ultrasound irradiation. And all physical properties of 6 were from the reactions under microwave irradiation using alpha-tosyloxysubstituted acetophen-ones (4) as starting materials.…”

Section: Methodsmentioning

confidence: 99%

“…The alpha-haloketones are a class of versatile reagents in organic synthesis; they are, however, difficult to obtain and highly lachrymatory, toxic, and not readily available and which have been replaced in this work by eco-friendly alpha-tosyloxyketones prepared from [hydroxy(tosyloxy)-iodo]benzene (HTIB) [12][13][14] and corresponding ketones in the refluxing acetonitrile.…”

Section: Introductionmentioning

confidence: 99%

An Unexpected and Green Synthetic Protocol for Ethyl 1-Aroyl/Aroylmethyl-5-methyl-3-methylthiopyrazole-4-carboxylates: High Regioselectivity in Alkylation and Acylation Reactions between N-1 and N-2 of a Pyrazole Ring

Wen

Wang

et al. 2005

Jnl Chinese Chemical Soc

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Two series, totaling twelve, of new compounds, ethyl 1-aroyl/(aroylmethyl)-5-methyl-3-methylthiopyrazole-4-carboxylates (5/6), have been synthesized via highly regioselectively acylation and alkylation reactions of ethyl 3-methyl-5-methylthio-1H-pyrazole-4-carboxylate (2a) with aroyl chloride (3) and eco-friendly reagents alpha-tosyloxysubstituted acetophenones (4), respectively, and a green protocol has been developed. The acylation reactions were carried out under ultrasound irradiation, and the alkylation reactions were under microwave irradiation and ultrasound irradiation, respectively. Conventional reaction conditions, as well as the use of alpha-bromosubstituted acetophenone (4¢) have also been applied in the synthesis of some randomly selected compounds in both series and have generated identical compounds correspondingly. Unexpected structures of compounds were unambiguously determined by X-ray crystallographic analysis.

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“…2,3,4 In particular, this renaissance in hypervalent iodine chemistry is captured beautifully in two recent scholarly treatises authored by Varvoglis. 3 These books provide the foundation of, and the inspiration for, the synthesis work outlined below.…”

Section: Introductionmentioning

confidence: 99%

Application of alkynyliodonium salts to natural products synthesis: A mini-review of recent work at Penn State

Feldman¹

2003

Arkivoc

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Total syntheses of the polycyclic natural products agelastatin A and pareitropone have been accomplished through the agency of alkynyliodonium salts. A review of these efforts, which emphasizes the value of hypervalent iodine chemistry in raising the molecular complexity of substrates upon chemical transformation, follows.Keywords: Agelastatin A, pareitropone, alkynyliodonium salts, natural products synthesis A desire to exploit the unique reactivity patterns offered by alkynyliodonium salts (5) has fueled a continuing effort to develop efficient syntheses of naturally occurring principles at Penn State. A progress report that details some recently completed projects in the areas of agelastatin A (1) and pareitropone (2) assembly is described herein.1 These advances owe much to the seminal contributions of many workers around the world, especially those recorded by the groups of Stang, Koser and Moriarity in the US, Ochiai and Kita in Japan, and, of course, by Anastasios Varvoglis' group at Thessaloniki. 2,3,4 In particular, this renaissance in hypervalent iodine chemistry is captured beautifully in two recent scholarly treatises authored by Varvoglis. 3 These books provide the foundation of, and the inspiration for, the synthesis work outlined below. Successful execution of total synthesis efforts often hinges on identifying solutions to problems of chemo-and stereoselectivity. Synthesis routes featuring alkynyliodonium salts are no exception, and key discoveries by Stang, 5 and independently, Ochiai, 6 have provided insight into how these types of selectivity issues might be addressed. In 1991, Stang and Zhdankin introduced PhI(CN)OTf (4) as a phenyliodonium transfer reagent of exquisite chemoselectivity in preparing alkynyliodonium units 5 from alkynylstannane precursors 3, Scheme 1. 5 Prior to this advance, it was unclear whether any of the existing iodonium transfer reagents could perform with the requisite selectivity that reaction with complex, multifunctional substrates demanded.

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Hypervalent Iodine Chemistry: 25 Years of Development at the University of Thessaloniki

Abstract: In λ 3 -iodanes of the PhIL 2 ( or PhILL') type, 1, L is an electronegative ligand which can be a halogen (F, Cl) or a group such as HO -, RO -,

Cited by 73 publications

References 61 publications

Spiro Cyclohexadienones from the Reaction of Phenolic Enaminone Derivatives with Hypervalent Iodine Reagents

Spiro Cyclohexadienones from the Reaction of Phenolic Enaminone Derivatives with Hypervalent Iodine Reagents

An Unexpected and Green Synthetic Protocol for Ethyl 1-Aroyl/Aroylmethyl-5-methyl-3-methylthiopyrazole-4-carboxylates: High Regioselectivity in Alkylation and Acylation Reactions between N-1 and N-2 of a Pyrazole Ring

Application of alkynyliodonium salts to natural products synthesis: A mini-review of recent work at Penn State

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