Hypervalent iodine oxidation products of papaverine and its microbial metabolites

Reddy, G. Chandrasekara

doi:10.1016/0040-4039(94)02426-c

“…The use of [bis(acyloxy)iodo]arenes for the oxidation of various organonitrogen compounds was thoroughly discussed in earlier reviews by Varvoglis. 9,13,19 More recent examples include the application of DIB for the preparation of N-oxides from nitroisoquinoline derivatives, 188 oxidations of hydrazones and similar carbonyl derivatives leading to regeneration of the carbonyl function, [189][190][191][192][193][194] Hofmann-type oxidation of carboxamides to carbamates, 195 oxidative amination of indoles with aromatic amines, 196 oxidation of papaverine, 197 and oxidatively assisted preparation of nitrogen heterocycles. 198,199 Thioacetals and thioketals are efficiently cleaved to carbonyl compounds with BTI under mild conditions.…”

Section: Oxidations With [Bis(acyloxy)iodo]arenesmentioning

confidence: 99%

Organic Polyvalent Iodine Compounds

Stang

¹

,

Zhdankin

²

1996

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“…This manifold is at the origin of certain phenol and naphthol dearomatization processes (Scheme 26, right). [22] A priori, such naphtholonium intermediates could also undergo a [3,3]-iodonio-sigmatropic rearrangement (Scheme 26, left), and in such cases, the resulting cationic intermediate could either engage in a double rearomatization to form an arylated naphthol, or stop at the a-arylquinone stage, as reported by Porco and co-workers for species 4 (Scheme 2 [9,10] ).…”

Section: Minireviewsmentioning

confidence: 73%

“…Examples of this phenomenon include an attempted generation of papaverine metabolites as well as efforts towards the valorization of resorcinol (Scheme 2, structures 2 and 3). [9] Most notably, Porco and co-workers repoted that the use of PhI(O 2 CCF 3 ) 2 in a related dearomatizative sequence led to the undesired C-arylated azaphilone 4 in 46 % yield. The formation of this side product was, once again, attributed to a [3,3]-sigmatropic rearrangement of the putative iodonium phenolate 5 (Scheme 2).…”

Section: Introductionmentioning

confidence: 99%

The Power of Iodane‐Guided C−H Coupling: A Group‐Transfer Strategy in Which a Halogen Works for Its Money

Chen

¹

,

Cuenca

²

,

Shafir

³

2020

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Hypervalent organoiodane reagents are ubiquitous in organic synthesis, both as oxidants and as electrophilic group‐transfer agents. In addition to these hallmark applications, a complementary strategy is gaining momentum that exploits the ability of λ3‐iodanes to undergo iodine‐to‐arene group transfer, for example, via iodonio‐Claisen‐type rearrangement processes. This Minireview discusses recent advances in the use of this method to access a variety of the C−H‐functionalized iodoarenes. While Section 2 is focused on the ortho C−H propargylation, allylation, and the more unusual para C−H benzylation, Section 3 is devoted to the C‐arylation of enol and phenol substrates. The accompanying discussion includes mechanistic considerations and goes into the synthetic applications of the final iodoarene cores. The Minireview concludes with further conceptual extensions of the method, including the use of non‐conventional coupling partners (for example, cyanoalkylation), improved access to λ3‐iodane building blocks, and the development of iterative approaches to polysubstituted iodoarenes.

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“…Kurzaufsätze certain phenol and naphthol dearomatization processes (Scheme 26, right). [22] A priori, such naphtholonium intermediates could also undergo a [3,3]-iodonio-sigmatropic rearrangement (Scheme 26, left), and in such cases, the resulting cationic intermediate could either engage in a double rearomatization to form an arylated naphthol, or stop at the a-arylquinone stage, as reported by Porco and co-workers for species 4 (Scheme 2 [9,10] ).…”

Section: Angewandte Chemiementioning

confidence: 73%

The Power of Iodane‐Guided C−H Coupling: A Group‐Transfer Strategy in Which a Halogen Works for Its Money

Chen

¹

,

Cuenca

²

,

Shafir

³

2020

View full text Add to dashboard Cite

Hypervalent organoiodane reagents are ubiquitous in organic synthesis, both as oxidants and as electrophilic group‐transfer agents. In addition to these hallmark applications, a complementary strategy is gaining momentum that exploits the ability of λ3‐iodanes to undergo iodine‐to‐arene group transfer, for example, via iodonio‐Claisen‐type rearrangement processes. This Minireview discusses recent advances in the use of this method to access a variety of the C−H‐functionalized iodoarenes. While Section 2 is focused on the ortho C−H propargylation, allylation, and the more unusual para C−H benzylation, Section 3 is devoted to the C‐arylation of enol and phenol substrates. The accompanying discussion includes mechanistic considerations and goes into the synthetic applications of the final iodoarene cores. The Minireview concludes with further conceptual extensions of the method, including the use of non‐conventional coupling partners (for example, cyanoalkylation), improved access to λ3‐iodane building blocks, and the development of iterative approaches to polysubstituted iodoarenes.

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Hypervalent iodine oxidation products of papaverine and its microbial metabolites

Cited by 18 publications

References 5 publications

Organic Polyvalent Iodine Compounds

Organic Polyvalent Iodine Compounds

The Power of Iodane‐Guided C−H Coupling: A Group‐Transfer Strategy in Which a Halogen Works for Its Money

The Power of Iodane‐Guided C−H Coupling: A Group‐Transfer Strategy in Which a Halogen Works for Its Money

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