RSC Harrison-Meldola Memorial Prize Lecture - Photoinduced Assembly of C-N Bonds

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Daniele Leonori
Photoinduced Assembly of C -N Bonds Dr Daniele Leonori School of Chemistry, University of Manchester, Manchester M13 9PL, UK Nitrogen -containing compounds are a privileged class of molecules, which have applications in medicines, agrochemicals, dyes and materials. This relevance makes the construction of C –N bonds an extremely active area of research. Nitrogen -radicals are versa tile synthetic intermediates that can engage in a broad range of chemical reactions. 1 However, the difficulties associated with their generation have somewhat thwarted their use in synthetic chemistry. Development of Photoinduced Radical -Transposition Reactions We have developed a class of easy -to -make oximes and hyroxy -amides that upon photoredox oxidation enable access to iminyl and amidyl radicals. 2,3 These species have been used in radical transposition reactions for the site -selective functionaliza tion of unactivated sp 3-carbons. These strategies have been applied to the deconstruction –functionalization of complex steroids (radical ring -opening) 2 and to the preparation of unnatural aminoacids (1,5 -HAT) .3 Development of Photoinduced Aromatic C –H Ami nation Reactions Aminated aromatics are a widespread motif in high -value products. In general, these structures are assemble d by Pd or Cu -catalysed cross -couplings between aryl halides/organoboron and amines. We have developed an umpolung approach where electrophilic amidyl and aminyl radicals are generated by photoredox reduction of electron poor N-aryloxy -amides and -amines. 4,5 These radical specie s undergo highly selective addition to a broad range of electron rich aromatics thus enabling direct C – H amination. References 1. Review: S. Z. Zard Chem. Soc. Rev. 2008 , 37 , 1603. 2. Angew. Chem. Int. Ed. 2018 , 57 , 744. 3. Angew. Chem. Int. Ed. 2018 , 57 , 12495. 4. J. Am. Chem. Soc. 2016 , 138 , 8092. 5. Angew. Chem. Int. Ed. 2017 , 56 , 14948. Download PDF

  • Venue

    Theatre C, Purdie

  • Date

    May 1, 2019

  • Time

    From: 14h00 To: 15h00

  • Sponsor

    Royal Society of Chemistry

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