Dual Hypervalent Iodine(III) Reagents and Photoredox Catalysis Enable Decarboxylative Ynonylation under Mild Conditions

Huang, Hanchu; Zhang, Guojin; Chen, Yiyun

doi:10.1002/anie.201502369

Cited by 199 publications

(75 citation statements)

References 63 publications

(52 reference statements)

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“…1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 4, 136.8, 134.1, 129.8, 129.6, 128.6, 125.6, 121.0, 117.56, 117.55, 93.0, 86.5, 55.4. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 137.2, 136.7, 134.24, 134.22, 129.6, 129.2, 128.7, 118.6, 91.6, 87.6. 2-(3-oxo-3-phenylprop-1-yn-1-yl)benzonitrile (4i): 9 The product was isolated by column chromatography on silica gel (ethyl acetate: petroleum ether = 1:20) as a white solid (12.5...…”

Section: Acs Paragon Plus Environmentmentioning

confidence: 99%

“…-1-phenylprop-2-yn-1-one (4l): 9 The product was isolated by column 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 …”

Section: -([11'-biphenyl]-4-yl)mentioning

confidence: 99%

“…)-1-phenylprop-2-yn-1-one (4h):9 The product was isolated by column chromatography on silica gel (ethyl acetate: petroleum ether = 1:50) as a light yellow solid(27.4 …”

mentioning

confidence: 99%

“…13 C NMR (151 MHz, CDCl 3 ) δ 177.3, 136.7, 135.6, 134.3, 131.5, 130.1, 129.6, 128.7, 128.0, 104.4, 96.0, 27.1, 18.9. HRMS calcd for C 25 H 25 OSi [M+H] + 369.1675; found:369.1673.1-phenyl-3-(p-tolyl)prop-2-yn-1-one(4f):10 The product was isolated by column chromatography on silica gel (ethyl acetate: petroleum ether = 1:50) as a white solid (35.7 mg, -methoxyphenyl)-1-phenylprop-2-yn-1-one (4g):9 The product was isolated by column chromatography on silica gel (ethyl acetate: petroleum ether = 1:50) as a yellow oil(11.8 mg, 25% …”

mentioning

confidence: 99%

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Transition-Metal-Free Synthesis of Ynones via Decarboxylative Alkynylation of α-Keto Acids under Mild Conditions

Wang¹,

Feng²,

Zhang³

et al. 2015

J. Org. Chem.

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Section: Acs Paragon Plus Environmentmentioning

confidence: 99%

Section: -([11'-biphenyl]-4-yl)mentioning

confidence: 99%

“…)-1-phenylprop-2-yn-1-one (4h):9 The product was isolated by column chromatography on silica gel (ethyl acetate: petroleum ether = 1:50) as a light yellow solid(27.4 …”

mentioning

confidence: 99%

mentioning

confidence: 99%

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Transition-Metal-Free Synthesis of Ynones via Decarboxylative Alkynylation of α-Keto Acids under Mild Conditions

Wang¹,

Feng²,

Zhang³

et al. 2015

J. Org. Chem.

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“…[ [36] fanden Li, Wang et al,dass eine sehr ähnliche lichtinduzierte decarboxylierende Alkinylierung von a-Ketosäuren problemlos auch ohne die Zugabe eines Photoredoxkatalysators durchführbar ist (Schema 21). [37] Bei dieser Reaktion wurden …”

Section: Radikalische Decarboxylierende Funktionalisierung Von Carbonunclassified

Durch sichtbares Licht induzierte decarboxylierende Funktionalisierung von Carbonsäuren und ihren Derivaten

2015

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Der radikalischen decarboxylierenden Funktionalisierung von Carbonsäuren und ihren Derivaten mithilfe von sichtbarem Licht wird seit einiger Zeit erhöhte Aufmerksamkeit zuteil, da sie ein neuartiges und effizientes Verfahren zur Knüpfung von C‐C‐ und C‐X‐Bindungen ist. Dieses Verfahren lässt sich unter milden Reaktionsbedingungen auf eine breite Palette von Substraten anwenden und toleriert eine Vielzahl funktioneller Gruppen. Die bei der Decarboxylierung gebildeten Radikale können nicht nur für photokatalytische Einzelumsetzungen, sondern auch für duale katalytische Kreuzkupplungen genutzt werden. Für Letzteres wird die Photoredoxkatalyse mit anderen katalytischen Verfahren verknüpft. Die jüngsten Fortschritte in diesem Forschungsbereich werden im Folgenden vorgestellt.

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Alkynylations and Vinylations

Hari

Nicolai

Waser

2018

Patai's Chemistry of Functional Groups

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Alkynes and alkenes are important building blocks in synthetic organic chemistry and related domains. Therefore, unceasing efforts have been invested to develop new methods to introduce these valuable functional groups. Traditionally, most alkynylation and alkenylation reactions have relied on the use of olefins and acetylenes as nucleophilic reacting species, limiting the accessible structural diversity. The discovery of the unique properties of hypervalent iodine has more recently significantly broadened the scope of electrophilic ethynylation and vinylation reactions. Alkynyl and alkenyl iodonium salts were first recognized as powerful reagents to install electrophilic acetylenes and olefins onto nucleophilic substrates under mild conditions. Their low stability has however narrowed the area of their applications. Since 2009, more stable cyclic benziodoxol(on)e reagents have shown their superiority as effective electrophilic alkynylating and alkenylating reagents in numerous metal-free and metal-catalyzed olefination and ethynylation reactions of carbon centered nucleophiles, radicals, and heteroatom nucleophiles. In this chapter, an overview of the progress in the field is presented, including a short summary of pioneering works, followed by a more in-depth description of recent results.

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Dual Hypervalent Iodine(III) Reagents and Photoredox Catalysis Enable Decarboxylative Ynonylation under Mild Conditions

Cited by 199 publications

References 63 publications

Transition-Metal-Free Synthesis of Ynones via Decarboxylative Alkynylation of α-Keto Acids under Mild Conditions

Transition-Metal-Free Synthesis of Ynones via Decarboxylative Alkynylation of α-Keto Acids under Mild Conditions

Durch sichtbares Licht induzierte decarboxylierende Funktionalisierung von Carbonsäuren und ihren Derivaten

Alkynylations and Vinylations

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