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3 article(s) from Walton, John C.

Preparative semiconductor photoredox catalysis: An emerging theme in organic synthesis

David W. Manley and
John C. Walton

Beilstein J. Org. Chem. 2015, 11, 1570–1582, doi:10.3762/bjoc.11.173

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Figure 1: Production and utilization of h⁺ and e^– by photoactivation of a semiconductor.

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Figure 2: Photoredox activity of TiO₂ with moist air.

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Scheme 1: TiO₂ promoted oxidation of phenanthrene [29].

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Scheme 2: SCPC assisted additions of allylic compounds to diazines and imines [40-42].

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Scheme 3: TiO₂ promoted addition and addition–cyclization reactions of tert-amines with electron-deficient al...

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Scheme 4: Reactions of amines promoted by Pt-TiO₂ [48,49].

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Scheme 5: P25 Promoted alkylations of N-phenylmaleimide with diverse carboxylic acids [53,54]. ^aAccompanied by R–R d...

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Scheme 6: SCPC cyclizations of aryloxyacetic acids with suitably sited alkene acceptors [54]. ^aYields in brackets...

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Scheme 7: TiO₂ promoted reactions of aryloxyacetic acids with maleic anhydride and maleimides [53,54].

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Scheme 8: Photoredox addition–cyclization reactions of aryloxyacetic and related acids promoted by maleimide [63]....

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Scheme 9: SCPC promoted homo-couplings and macrocyclizations with carboxylic acids [64].

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Scheme 10: TiO₂ promoted alkylations of alkenes with silanes [66] and thiols [67].

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Scheme 11: TiO₂ reduction of a nitrochromenone derivative [70].

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Scheme 12: TiO₂ mediated hydrodehalogenations and cyclizations of organic iodides [71].

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Scheme 13: TiO₂ promoted hydrogenations of maleimides, maleic anhydride and aromatic aldehydes [79].

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Scheme 14: Mechanistic sketch of SCPC hydrogenation of aryl aldehydes.

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Published 09 Sep 2015

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Interplay of ortho- with spiro-cyclisation during iminyl radical closures onto arenes and heteroarenes

Roy T. McBurney and
John C. Walton

Beilstein J. Org. Chem. 2013, 9, 1083–1092, doi:10.3762/bjoc.9.120

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Figure 1: O-Ethoxycarbonyl oximes prepared.

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Scheme 1: Photochemical reactions of biphenyl oxime carbonates.

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Figure 2: EPR spectrum during photolysis of 1f in t-BuPh at 240 K. Top (black): experimental spectrum. Bottom...

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Figure 3: EPR spectrum during photolysis of 2a in t-BuPh at 230 K. Top (blue): experiment; bottom (red): simu...

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Scheme 2: Ring closure of iminyl radicals derived from 2a,b.

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Figure 4: DFT computed structures for 5a, 11a and their cyclisation transition states (TS). Top line: spin de...

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Published 04 Jun 2013

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EPR and pulsed ENDOR study of intermediates from reactions of aromatic azides with group 13 metal trichlorides

Giorgio Bencivenni,
Riccardo Cesari,
Daniele Nanni,
Hassane El Mkami and
John C. Walton

Beilstein J. Org. Chem. 2010, 6, 713–725, doi:10.3762/bjoc.6.84

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Scheme 1: Organic azides studied.

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Scheme 2: Reaction of 4-substituted-phenyl azides with GaCl₃.

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Figure 1: EPR spectra after treatment of azide 2 with MCl₃. (a) AlCl₃ in DCM; 1st derivative spectrum at 300 ...

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Figure 2: EPR spectrum after treatment of tetra-deuterated azide 3 with AlCl₃. Top: 2nd derivative spectrum a...

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Figure 3: EPR spectra after treatment of azide 1 with AlCl₃. (a) 1st derivative spectrum in DCM at 280 K. (b)...

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Figure 4: EPR spectra after GaCl₃ and InCl₃ reactions of azide 6. (a) 1st derivative spectrum from 6 and GaCl₃...

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Scheme 3: Dimer and trimer radical cations.

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Figure 5: EPR spectra after GaCl₃- and InCl₃-promoted reactions of 2-methoxyphenyl azide 5. (a) 1st derivativ...

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Figure 6: EPR spectra after In-, Ga- and Al-promoted reactions of azide 8. (a) intermediate from InCl₃ treatm...

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Figure 7: Experimental and simulated Davies ENDOR spectrum after the Ga-promoted reaction of azide 6 recorded...

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Figure 8: DFT structures and SOMOs for dimer and trimer radical cations.

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Scheme 4: Possible mechanism of formation of aromatic amines.

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Scheme 5: Possible mechanism for dimer and trimer formation.

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Published 09 Aug 2010

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