Light-catalyzed Organic Reactions. I. The Reaction of Carbonyl Compounds with 2-Methyl-2-butene in the Presence of Ultraviolet Light

Büchi, G.; Inman, Charles G.; Lipinsky, E.S.

doi:10.1021/ja01646a024

Cited by 318 publications

(136 citation statements)

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“…33 Numerous photoinduced processes have been successfully initiated by using n, π* triplet-excited ketones, such as hydrogen abstraction, 34 oxetane formation (Paterno−Buchi reaction), 35 photocyclization, 36 and the Norrish reactions. 37 As depicted in Figure 1a, acetone has a strong absorption band in the ultraviolet range below 330 nm.…”

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confidence: 99%

Simple and Clean Photoinduced Aromatic Trifluoromethylation Reaction

et al. 2016

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We describe a simple, metal-and oxidantfree photochemical strategy for the direct trifluoromethylation of unactivated arenes and heteroarenes under either ultraviolet or visible light irradiation. We demonstrated that photoexcited aliphatic ketones, such as acetone and diacetyl, can be used as promising low-cost radical initiators to generate CF 3 radicals from sodium triflinate efficiently. The broad utility of this strategy and its benefit to medicinal chemistry are demonstrated by the direct trifluoromethylation of unprotected bidentate chelating ligand, xanthine alkaloids, nucleosides, and related antiviral drug molecules.

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confidence: 99%

Simple and Clean Photoinduced Aromatic Trifluoromethylation Reaction

et al. 2016

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“…First described by Paternò, 4 the reaction attracted renewed interest following the mechanistic studies of Büchi et al which showed that the reaction proceeded via a 1,4-biradical intermediate. 5 Since these initial works, numerous studies have been devoted to exploring mechanistic details of several PB reactions with differing substrates. [6][7][8][9][10][11][12][13][14][15][16][17] Reaction between the carbonyl and the alkene can proceed by attack at either the C or the O atom of the carbonyl group, forming one of two possible biradical intermediates.…”

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confidence: 99%

Tracking a Paternò–Büchi Reaction in Real Time Using Transient Electronic and Vibrational Spectroscopies

et al. 2014

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“…In this study, a photoaddition reaction between an aldehyde (or ketone) and an alkene known as Paternò-Büchi (PB) reaction [42][43][44][45] is considered. Its mechanism has been studied extensively both experimentally and theoretically [46][47][48][49][50][51][52][53][54].…”

Section: Introductionmentioning

confidence: 99%

Exploring Pathways of Photoaddition Reactions by Artificial Force Induced Reaction Method: A Case Study on the Paternò–Büchi Reaction

Maeda

Taketsugu

Morokuma

2013

Zeitschrift für Physikalische Chemie

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The present study demonstrates a priori prediction of the mechanism of Paternò-Büchi (PB) reaction by automated search for reaction pathways using the artificial force induced reaction (AFIR) method, for the simplest set of reactants, H 2 CO + C 2 H 4 . The search found all previously suggested pathways automatically without using any guess about the reaction mechanism. Even the reaction product was not assumed. In addition, a comprehensive view of the reaction path network obtained in the present extensive search gave new insights into the mechanism. Barriers on excited states explained the preference of the initial bonding sites. A seam of crossing between the lowest triplet and first singlet excited state is suggested to make a significant contribution to an intersystem crossing and the reaction mechanism of the present system.

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Light-catalyzed Organic Reactions. I. The Reaction of Carbonyl Compounds with 2-Methyl-2-butene in the Presence of Ultraviolet Light

Cited by 318 publications

References 0 publications

Simple and Clean Photoinduced Aromatic Trifluoromethylation Reaction

Simple and Clean Photoinduced Aromatic Trifluoromethylation Reaction

Tracking a Paternò–Büchi Reaction in Real Time Using Transient Electronic and Vibrational Spectroscopies

Exploring Pathways of Photoaddition Reactions by Artificial Force Induced Reaction Method: A Case Study on the Paternò–Büchi Reaction

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