Light‐Mediated Deoxygenation of Alcohols with a Dimeric Gold Catalyst

McCallum, Terry; Slavko, Ekaterina; Morin, Mathieu; Barriault, Louis

doi:10.1002/ejoc.201403351

Cited by 49 publications

(23 citation statements)

References 45 publications

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“…79 It has been reported that binuclear gold complexes can also perform photoredox catalysis; this strategy has been applied in radical additions to π systems 80 functional group inter-conversions 81 and other radical coupling reactions. 82 …”

Section: Dual Catalysis With Goldmentioning

confidence: 99%

Recent synthetic additions to the visible light photoredox catalysis toolbox

et al. 2015

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The boom in visible light photoredox catalysis (VLPC) research has demonstrated that this novel synthetic approach is here to stay. VLPC enables reactive radical intermediates to be catalytically generated at ambient temperature, a feat not generally allowed through traditional pyrolysis- or radical initiator-based methodologies. VLPC has vastly extended the range of substrates and reaction schemes that have been traditionally the domain of radical reactions. In this review the photophysics background of VLPC will be briefly discussed, followed by a report on recent inroads of VLPC into decarboxylative couplings and radical C-H functionalization of aromatic compounds. The bulk of the review will be dedicated to advances in synergistic catalysis involving VLPC, namely the combination of photoredox catalysis with organocatalysis, including β-functionalization of carbonyl groups, functionalization of weak aliphatic C-H bonds, and anti-Markovnikov hydrofunctionalization of alkenes; dual catalysis with gold or with nickel, photoredox catalysis as an oxidation promoter in transition metal catalysis, and acid-catalyzed enantioselective radical addition to π systems.

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Section: Dual Catalysis With Goldmentioning

confidence: 99%

Recent synthetic additions to the visible light photoredox catalysis toolbox

et al. 2015

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“…The mechanism of these reactions via a photoredox dehalogenation–protonation process is established 18,19. Our Stern–Volmer experiments demonstrated the occurrence of the same catalytic cycle in which the transformation was triggered by reductive quenching of the photoredox catalyst (see the ESI†).…”

Section: Resultsmentioning

confidence: 56%

“…Alkyl halides (X) are an important class of readily accessible starting substrates in organic synthesis 16. Since Tanaka and co-workers introduced the visible light-driven reductive dehalogenation of benzyl bromide to benzene in 1984,17 the groups of Kellogg,18 a Fukuzumi,18 b Stephenson,18c–e Zeitler,18 f and Hisaeda18 g and so on18h–o have accomplished the transformation of diverse alkyl halides to alkanes via photoredox catalysis with tertiary amines as the reductant. This conceptual strategy was developed by the Reiser group19 by establishing an alternative reductive system, i.e.…”

Section: Introductionmentioning

confidence: 99%

Enantioselective photoredox dehalogenative protonation

et al. 2019

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“…In another report, the described method was coupled with a photomediated bromination strategy of alcohols (22)(23)(24)(25)(26) using CBr 4 , leading to an efficient 2-step, one-pot, photomediated deoxygenation protocol (Scheme 4, d). 14 Substrates bearing amino acids, 5-exo-trig and dig amenable moieties, functionalized arenes and sugars were well tolerated, giving products 7, 10, and 30-32 in 70-85% yield.…”

Section: Account Syn Lettmentioning

confidence: 98%

Thieme Chemistry Journals Awardees – Where Are They Now? What’s Golden: Recent Advances in Organic Transformations Using Photoredox Gold Catalysis

McCallum

Rohe

Barriault

2016

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Light-mediated photoredox transformations have become commonplace in contemporary catalysis research and design. Excitedstate redox catalysts trigger photoinduced electron transfers (PET) through oxidative or reductive quenching modes, allowing access to one-electron variations of classic radical reactions and the discovery of new transformations in organic chemistry. Herein, the use of Au-based photoredox catalysts containing powerful redox properties along with the emergence of dual catalyzed organic transformations involving photoredox catalysis and Au complexes for the Au(I)/Au(III) redox couple without use of stoichiometric oxidants will be discussed. 1 Principles of Photochemistry and Gold 2 Photoredox Transformations with Dimeric Gold Complexes 3 Dual Catalysis Involving Au(I)/Au(III) Redox Cycles 4 Concluding Remarks

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Light‐Mediated Deoxygenation of Alcohols with a Dimeric Gold Catalyst

Abstract: A new protocol for the reductive deoxygenation of primary alcohols was explored. This photomediated method combines a novel approach to bromination of alcohols merged with the powerful reducing capability of [Au 2 (dppm) 2 ]Cl 2

Cited by 49 publications

References 45 publications

Recent synthetic additions to the visible light photoredox catalysis toolbox

Recent synthetic additions to the visible light photoredox catalysis toolbox

Enantioselective photoredox dehalogenative protonation

Thieme Chemistry Journals Awardees – Where Are They Now? What’s Golden: Recent Advances in Organic Transformations Using Photoredox Gold Catalysis

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