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A Mechanism Study for Self-Cleaving Chlorotetrafluoroethylsulfinyl (-SOCF2CF2Cl)-Directed Pd(II)-Catalyzed C-H Activation.

A mechanism study for Pd(II)-catalyzed C(sp3)-H activation using a self-cleaving chlorotetrafluoroethylsulfinyl (-SOCF2CF2Cl) auxiliary as a directing group is reported. Mechanistic studies reveal that (1) the auxiliary group is crucial for C(sp3)-H activation, (2) the reaction undergoes a C(sp3)-H olefination-Michael addition-removal of the auxiliary sequence, (3) the removal of the auxiliary (SORf) is most likely the alcoholic solvolysis of the -SOCF2CF2Cl group on the N-tri-substituted sulfonamides, and (4) the C(sp3)-H cleavage is involved in the rate-determining step.