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Palladium‐Catalyzed Divergent Cyclopropanation by Regioselective Solvent‐Driven C(sp 3 )−H Bond Activation
Author(s) -
Chung Da Sol,
Lee Jae Sung,
Ryu Ho,
Park Jiyong,
Kim Hyunjoong,
Lee Joo Hyun,
Kim U Bin,
Lee Won Koo,
Baik MuHyun,
Lee Sanggi
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201809133
Subject(s) - regioselectivity , palladium , chemistry , cyclopropanation , catalysis , solvent , solvent effects , photochemistry , activation energy , molecule , medicinal chemistry , stereochemistry , organic chemistry
Reported is a tandem palladium‐catalyzed Heck/regioselective C(sp 3 )−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‐alkylPd II 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‐alkylPd II intermediate.
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