Photochemically induced radical alkenylation of C(sp<sup>3</sup>)–H bonds

Amaoka, Yuuki; Nagatomo, Masanori; Watanabe, Mizuki; Tao, Katsumi; Kamijo, Shunsuke; Inoue, M.

doi:10.1039/c4sc01631a

Cited by 111 publications

(53 citation statements)

References 78 publications

(2 reference statements)

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“…In contrast, isomeric 1,2‐bis(phenylsulfonyl)ethylene enabled the direct alkenylation of C(sp 3 )–H bonds in ethers, alcohols, amides, and alkanes under irradiation in the presence of benzophenone (BP; 1 equiv.) . A dual catalytic strategy for the carboxylation of allylic C–H bonds, promoted by a system composed of a xanthone derivative and a copper complex, has been reported.…”

Section: Direct Hat Approachesmentioning

confidence: 99%

Hydrogen Atom Transfer (HAT): A Versatile Strategy for Substrate Activation in Photocatalyzed Organic Synthesis

2017

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The adoption of hydrogen atom transfer (HAT) in a photocatalytic approach, in which an excited catalyst is responsible for substrate activation, offers unique opportunities in organic synthesis, enabling the straightforward activation of R–H (R = C, Si, S) bonds in desired reagents. Either a direct strategy, based on the intrinsic reactivity of a limited number of photocatalysts in the excited state, or an indirect one, in which a photocatalytic cycle is used for the generation of a thermal hydrogen abstractor, can be exploited. This microreview summarizes the most recent advances (mainly from the last two years) in this rapidly developing area of research, collecting the selected examples according to the nature of the species promoting the HAT process. From the synthetic point of view, this area has led to the development of a plethora of strategies for C–C, C–Si, C–N, C–S, and C–halogen (particularly, fluorine) bond formation, as well as for oxidation reactions.

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Section: Direct Hat Approachesmentioning

confidence: 99%

Hydrogen Atom Transfer (HAT): A Versatile Strategy for Substrate Activation in Photocatalyzed Organic Synthesis

2017

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“…The same year, Xiang and Fuchs extended their method by incorporation of vinyl triflones as the alkenylation reagent via an azobisisobutyronitrile (AIBN)‐catalyzed process [15b] . Later, Inoue and co‐workers introduced a stoichiometric photocatalytic method employing benzophenone for the direct alkynylation [15c] and alkenylation [15d] of 2‐pyrrolidinone (Scheme 1C). Very recently, Paul and Guin took advantage of the main activation mode of benzophenone‐derived triplets, in order to initiate a HAT process (Scheme 1D) [15e] .…”

Section: Introductionmentioning

confidence: 99%

Phenylglyoxylic Acid: An Efficient Initiator for the Photochemical Hydrogen Atom Transfer C−H Functionalization of Heterocycles

et al. 2020

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, [a] Nikolaos F. Nikitas, [a] Errika Voutyritsa, [a] Dimitrios I. Tzaras, [a] Nikolaos Kaplaneris, [a] and Christoforos G. Kokotos* [a] CÀ H functionalization at the α-position of heterocycles has become a rapidly growing area of research. Herein, a cheap and efficient photochemical method was developed for the CÀ H functionalization of heterocycles. Phenylglyoxylic acid (PhCO-COOH) could behave as an alternative to metal-based catalysts and organic dyes and provided a very general and wide array of photochemical CÀ H alkylation, alkenylation, and alkynylation, as well as CÀ N bond forming reaction methodologies. This novel, mild, and metal-free protocol was successfully employed in the functionalization of a wide range of CÀ H bonds, utilizing not only O-or N-heterocycles, but also the less studied S-heterocycles.

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“…In 2014, Inoue and Kamijo's group reported a metal-free sulfonylalkenylation reaction of proline derivative with bis(phenylsulfonyl)ethylene in quantitive yield under the photo-irradiation conditions (Scheme 32) [74]. The sulfonylalkene could be easily converted to prenyl alcohol and pyrrole derivative, which gives this transformation possess extended synthetic utility.…”

Section: C-h Alkenylationmentioning

confidence: 99%

Recent Advances in Rapid Synthesis of Non-proteinogenic Amino Acids from Proteinogenic Amino Acids Derivatives via Direct Photo-Mediated C–H Functionalization

Yuan

Liu

et al. 2020

Molecules

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Non-proteinogenic amino acids have attracted tremendous interest for their essential applications in the realm of biology and chemistry. Recently, rising C–H functionalization has been considered an alternative powerful method for the direct synthesis of non-proteinogenic amino acids. Meanwhile, photochemistry has become popular for its predominant advantages of mild conditions and conservation of energy. Therefore, C–H functionalization and photochemistry have been merged to synthesize diverse non-proteinogenic amino acids in a mild and environmentally friendly way. In this review, the recent developments in the photo-mediated C–H functionalization of proteinogenic amino acids derivatives for the rapid synthesis of versatile non-proteinogenic amino acids are presented. Moreover, postulated mechanisms are also described wherever needed.

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Photochemically induced radical alkenylation of C(sp³)–H bonds

Cited by 111 publications

References 78 publications

Hydrogen Atom Transfer (HAT): A Versatile Strategy for Substrate Activation in Photocatalyzed Organic Synthesis

Hydrogen Atom Transfer (HAT): A Versatile Strategy for Substrate Activation in Photocatalyzed Organic Synthesis

Phenylglyoxylic Acid: An Efficient Initiator for the Photochemical Hydrogen Atom Transfer C−H Functionalization of Heterocycles

Recent Advances in Rapid Synthesis of Non-proteinogenic Amino Acids from Proteinogenic Amino Acids Derivatives via Direct Photo-Mediated C–H Functionalization

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Photochemically induced radical alkenylation of C(sp3)–H bonds

Cited by 111 publications

References 78 publications

Hydrogen Atom Transfer (HAT): A Versatile Strategy for Substrate Activation in Photocatalyzed Organic Synthesis

Hydrogen Atom Transfer (HAT): A Versatile Strategy for Substrate Activation in Photocatalyzed Organic Synthesis

Phenylglyoxylic Acid: An Efficient Initiator for the Photochemical Hydrogen Atom Transfer C−H Functionalization of Heterocycles

Recent Advances in Rapid Synthesis of Non-proteinogenic Amino Acids from Proteinogenic Amino Acids Derivatives via Direct Photo-Mediated C–H Functionalization

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Photochemically induced radical alkenylation of C(sp³)–H bonds