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Reporter:Junting Hong Date: 2016-9-23

Reporter:Junting Hong Date: 2016-9-23. Background. C onventional metal carbene transformations ( Rh carbene and Cu carbene ). Pd-catalyzed cross-coupling of diazo compounds. T he formation of two separate C-C bonds in a carbenic center are indeed possible. Investigation. key issues

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Reporter:Junting Hong Date: 2016-9-23

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  1. Reporter:Junting Hong Date: 2016-9-23

  2. Background • Conventional metal carbene transformations(Rh carbene and Cu carbene) • Pd-catalyzed cross-coupling of diazo compounds • The formation of two separate C-C bonds in a carbenic center are indeed possible.

  3. Investigation • key issues • possible side reactions: overinsertion, direct coupling, and H- elimination.

  4. Optimization Studies Results discussion Slow addition of 3a can not improve the reaction.(1,2) Brombenzene(2,3,4) Ligand: Xphos(3,5,6,7) CuI(3,8) Solvent: Toluene(3,9,10,11) The ratio of the substrates: 1:1:1(3,12,13,14)

  5. Scope N-tosylhydrazone component aromatic bromide component terminal alkyne

  6. A Plausible Mechanism

  7. Overview • A three-component coupling of N-tosylhydrazones, terminal alkynes, and aryl halides was developed. • Via a sequential palladium carbene migratory insertion and reductive elimination process, two separate C-C bonds on a carbenic carbon can be formed. • To incorporate Pd carbene migratory insertion with transmetalation of various metal compounds is possible .

  8. My Work

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