Metal-free direct alkylation of unfunctionalized allylic/benzylic sp<sup>3</sup>C–H bonds via photoredox induced radical cation deprotonation

Zhou, Rong; Liu, Haiwang; Tao, Hairong; Yu, Xingjian; Wu, Jie

doi:10.1039/c7sc00953d

Cited by 137 publications

(70 citation statements)

References 46 publications

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“…In 2015, the MacMillan group reported a direct arylation of allylic sp 3 C−H bonds via the combination of photoredox and thiol organic catalysis that promotes a hydrogen atom transfer (HAT) to access allylic radicals. Recently, Wu and co‐workers reported the metal‐free direct alkylation of unfunctionalized allylic sp 3 C−H bonds through a photoredox‐induced radical cation deprotonation (Scheme ).…”

Section: C(sp3)−h Bond Functionalizationmentioning

confidence: 99%

Visible Light‐Induced C−H Bond Functionalization: A Critical Review

et al. 2018

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In recent years,v isible-light-induced C À H bond functionalization has become an emerging field at the forefront of organic chemistry.I nag eneral sense,t hese approaches rely on the capability of metal complexes ando rganic dyes to convert visible light into chemical energy by engaging in single-electron transfer with organic substrates,t husg enerating reactivei ntermediates.T hisr eview covers most of the strategies involving visible light-induced benzylic and non-benzylic

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Section: C(sp3)−h Bond Functionalizationmentioning

confidence: 99%

Visible Light‐Induced C−H Bond Functionalization: A Critical Review

et al. 2018

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“…Our recently developed "stop-flow" micro-tubing (SFMT) reactor, with its enhanced light penetration efficiency,was applied when the conversions were low in batch reactors. [14] Employing Et 3 SiH and Me 2 PhSiH as two representative silane reagents,adiverse range of electron-deficient alkenes were examined. As depicted in Scheme 2a,acrylates with different steric and electronic properties were suitable substrates (4)(5)(6)(7)(8)(9)(10)(11)(12), and functional groups such as silane (10), ether (11), and epoxide (12)m oieties were tolerated.…”

Section: Visible-light-mediated Metal-free Hydrosilylation Of Alkenesmentioning

confidence: 99%

Visible‐Light‐Mediated Metal‐Free Hydrosilylation of Alkenes through Selective Hydrogen Atom Transfer for Si−H Activation

et al. 2017

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Although there has been significant progress in the development of transition-metal-catalyzed hydrosilylations of alkenes over the past several decades,m etal-free hydrosilylation is still rare and highly desirable.H erein, we report ac onvenient visible-light-driven metal-free hydrosilylation of both electron-deficient and electron-richalkenes that proceeds through selective hydrogen atom transfer for Si À Ha ctivation. The synergistic combination of the organophotoredoxcatalyst 4CzIPN with quinuclidin-3-yl acetate enabled the hydrosilylation of electron-deficient alkenes by selective SiÀHa ctivation while the hydrosilylation of electron-rich alkenes was achieved by merging photoredoxa nd polarity-reversal catalysis.

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“…Although much progress has been achieved, the developed systems usually require stoichiometric peroxides and a large excess of the C-H partner (over 40 equivalents of the alkanes), and the substrate scopes are limited to simple hydrocarbons and aromatic aldehydes. In pursuing methods for olefin construction [25][26][27] and photomediated C-H bond functionalization [28][29][30][31] , we aspired to develop an auxiliary-free and oxidant-free strategy for C sp3 -H and C sp2 (O)-H alkenylation with the C-H substrate as the limiting reagent (Fig. 1c).…”

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Photoinduced site-selective alkenylation of alkanes and aldehydes with aryl alkenes

et al. 2020

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The dehydrogenative alkenylation of C-H bonds with alkenes represents an atom-and stepeconomical approach for olefin synthesis and molecular editing. Site-selective alkenylation of alkanes and aldehydes with the C-H substrate as the limiting reagent holds significant synthetic value. We herein report a photocatalytic method for the direct alkenylation of alkanes and aldehydes with aryl alkenes in the absence of any external oxidant. A diverse range of commodity feedstocks and pharmaceutical compounds are smoothly alkenylated in useful yields with the C-H partner as the limiting reagent. The late-stage alkenylation of complex molecules occurs with high levels of site selectivity for sterically accessible and electron-rich C-H bonds. This strategy relies on the synergistic combination of direct hydrogen atom transfer photocatalysis with cobaloxime-mediated hydrogen-evolution cross-coupling, which promises to inspire additional perspectives for selective C-H functionalizations in a green manner.

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Metal-free direct alkylation of unfunctionalized allylic/benzylic sp³C–H bonds via photoredox induced radical cation deprotonation

Abstract: An unprecendented direct alkylation of unfunctionalized allylic/benzylic sp3 C–H bonds via photoredox induced radical cation deprotonation is disclosed.

Cited by 137 publications

References 46 publications

Visible Light‐Induced C−H Bond Functionalization: A Critical Review

Visible Light‐Induced C−H Bond Functionalization: A Critical Review

Visible‐Light‐Mediated Metal‐Free Hydrosilylation of Alkenes through Selective Hydrogen Atom Transfer for Si−H Activation

Photoinduced site-selective alkenylation of alkanes and aldehydes with aryl alkenes

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Metal-free direct alkylation of unfunctionalized allylic/benzylic sp3C–H bonds via photoredox induced radical cation deprotonation

Abstract: An unprecendented direct alkylation of unfunctionalized allylic/benzylic sp3 C–H bonds via photoredox induced radical cation deprotonation is disclosed.

Cited by 137 publications

References 46 publications

Visible Light‐Induced C−H Bond Functionalization: A Critical Review

Visible Light‐Induced C−H Bond Functionalization: A Critical Review

Visible‐Light‐Mediated Metal‐Free Hydrosilylation of Alkenes through Selective Hydrogen Atom Transfer for Si−H Activation

Photoinduced site-selective alkenylation of alkanes and aldehydes with aryl alkenes

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Metal-free direct alkylation of unfunctionalized allylic/benzylic sp³C–H bonds via photoredox induced radical cation deprotonation