Metal-free C(sp3)−H functionalization: Oxidative carbo-oxygenation of a-diazo carbonyls via radical dediazotization

Nan-Nan Wang, Wen-Juan Hao, Tian-Shu Zhang, Guigen Li,* Ya-Nan Wu, Shu-Jiang Tu,* Bo Jiang*

A novel three-component carbo-oxygenation of a-diazo carbonyls for flexible synthesis of unprecedented alpha-aminooxy-beta-amino ketones has been established through metal-free C(sp3)−H functionalization from readily accessible N,N-dimethylanilines and N-hydroxyphthalimide. The reaction pathway involves in situ-generated phthalimide N-oxyl radical-triggered dediazotization / radical coupling sequence, leading to C-O and C-C bond formation.

Chem. Commun. 2016, 52, 5144-5147

Synergistic rhodium/copper catalysis: Synthesis of 1,3-enynes and N-aryl enaminones

Nan-Nan Wang, Lei-Rong Huang, Wen-Juan Hao,* Tian-Shu Zhang, Guigen Li, Shu-Jiang Tu,* Bo Jiang*

Synergistic rhodium/copper catalysis enables new three-component coupling reactions of terminal alkynes and alpha-diazoketones or/and arylamines, allowing dediazotized carbene C−H insertion for the synthesis of functionalized 1,3-enynes and N-aryl enaminones with high stereoselectivity. The synthetic utility of these transformations results in subsequent C–C or/and C–N bond-forming reactions to effectively build up functional molecules with potential significance

 Org. Lett. 2016, 18,  1298-1301