Palladium-Catalyzed Divergent Cyclopropanation by Regioselective Solvent-Driven C(sp3 )-H Bond Activation
Da Sol Chung1, Jae Sung Lee2, Ho Ryu3,4
1Department of Chemistry and Nanoscience (BK21 PLUS), Ewha Womans University, Seoul, 03760, Republic of Korea.
Abstract:
Reported is a tandem palladium-catalyzed Heck/regioselective C(sp3 )-H activation reaction for the divergent synthesis of spiro- and fused-cyclopropanated indolines from N-methallylated 2-bromoarylamides. The regioselectivity of the C-H bond activation in the σ-alkylPdII intermediate is controlled by the solvent used. DFT calculations suggest that the polarity of solvent molecules could influence the transition-state energy, leading to a bifurcation of the C-H bond activation in the σ-alkylPdII intermediate.
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