Palladium-Catalyzed Tandem Divergent Cyclopropanation via Solvent-Driven Regioselective C(sp3)-H Bond Activation.

We report a palladium-catalyzed tandem Heck/regioselective C(sp3)-H activation for divergent synthesis of spiro- and fused-cyclopropanated indolines from N-methallylated 2-bromoarylamides. The regioselectivity of the C-H bond activation of σ-alkylPd(II) intermediate could be controlled by the choice of 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 by the σ-alkylPd(II) intermediate.
PMID: 30276944 [PubMed - as supplied by publisher]

Source: Angewandte Chemie - October 1, 2018 Category: Chemistry Authors: Chung DS, Lee JS, Ryu H, Park J, Kim H, Lee JH, Kim UB, Lee WK, Baik MH, Lee SG Tags: Angew Chem Int Ed Engl Source Type: research