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Pd(II)−Catalyzed Non‐Directed Benzylic C(sp3)−H Activation: Cascade C(sp3)−S Bond Cleavage to Access Benzaldehydes from Benzylphenyl Sulfides and Sulfoxides

Von Wiley-VCH zur Verfügung gestellt

Palladium(II)−catalyzed inert benzylic C(sp3)−H bond activation of benzylphenyl sulfides and sulfoxides has been developed that affords a series of benzaldehydes via cascade C(sp3)−S bond cleavage in one pot under a mutual conditions. This provides a strategy for late–stage site–selective C(sp3)–H bond functionalization via regiospecific activation of less reactive benzylic C(sp3)–H bond as compared to heteroatom–directed more reactive C(sp2)–H bond. The catalyst is recycled under aerobic condition.


Abstract

A novel, efficient and mutual strategy on Pd(II)−catalyzed inert benzylic C(sp3)−H bond activation of benzylphenyl sulfides and sulfoxides has been developed that provides access to a series of benzaldehydes via cascade C(sp3)−S bond cleavage in one pot. The highlight of this protocol is the regiospecific activation of less reactive benzylic C(sp3)−H bond as compared to heteroatom-directed more reactive C(sp2)−H bond, thus providing a strategy for late−stage site−selective C(sp3)−H bond functionalization. The reaction proceeds under air in moderate to good yields with excellent functional groups tolerance.

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