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Ecofriendly N-heterocyclic carbene (NHC) organocatalysis can control the N 1 -functionalization (aza-Michael addition) and C 3 -functionalization (Morita-Baylis-Hillman reaction, MBH) of isatins in the absence of (1) a protecting group, (2) a stoichiometric reagent, and (3) heat energy. The challengeable N 1 -functionalization of N-unsubstituted isatins into N-substituted (NS) isatins was realized through 10 mol % NHC and 10 mol % 1,8-diazabicyclo[5.4.0]undec-7-ene catalysts within 10 min with up to 98% isolation yield. The subsequent MBH adducts of as-synthesized NS-isatins (N 1 /C 3 -functionalization) was perfectly acquired in 10 mol % NHC and 10 mol % 1,4-diazabicyclo[2.2.2]octane catalysis within 30 min with superiority to C 3 /N 1 -functionalization (MBH/aza-Michael). For guiding the application to a versatile druggable isatin library, the NHC catalysis was compared with reported functionalization of isatins in view of green chemistry principles including solvent scoring of ACS GCI pharmaceutical roundtable, E-factor, atom economy, and so on.

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Highly Efficient and Practical N-Heterocyclic Carbene Organocatalyzed Chemoselective N<sub>1</sub>/C<sub>3</sub>-Functionalization of Isatins with Green Chemistry Principles

Highly Efficient and Practical N-Heterocyclic Carbene Organocatalyzed Chemoselective N1/C3-Functionalization of Isatins with Green Chemistry Principles

Highly Efficient and Practical N-Heterocyclic Carbene Organocatalyzed Chemoselective N₁/C₃-Functionalization of Isatins with Green Chemistry Principles