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The first Pd(II)-catalyzed sp(3) C-H olefination reaction has been developed using N-arylamide directing groups. Following olefination, the resulting intermediates were found to undergo rapid 1,4-addition to give the corresponding gamma-lactams. Notably, this method was effective with substrates containing alpha-hydrogen atoms and could be applied to effect methylene C-H olefination of cyclopropane substrates.

Pd(II)-Catalyzed Olefination of sp3 C−H Bonds

Pd(II)-Catalyzed Olefination of sp³ C−H Bonds