Pd(II)−Catalyzed Non‐Directed Benzylic C(sp3)−H Activation: Cascade C(sp3)−S Bond Cleavage to Access Benzaldehydes from Benzylphenyl Sulfides and Sulfoxides. Issue 12 (12th September 2022)

• Record Type: Journal Article
• Authors: Joshi, Asha; Iqbal, Zafar; Kandwal, Pankaj; De, Saroj Ranjan
• Is Part Of: Asian journal of organic chemistry. Volume 11:Issue 12(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-09-12
• Subjects: benzaldehydes -- benzylphenyl sulfide/sulfoxide -- cascade C−S bond cleavage -- inert C(sp3)−H activation -- transition-metal−catalyst; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.202200400
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract: A novel, efficient and mutual strategy on Pd(II)−catalyzed inert benzylic C(sp 3 )−H bond activation of benzylphenyl sulfides and sulfoxides has been developed that provides access to a series of benzaldehydes via cascade C(sp 3 )−S bond cleavage in one pot. The highlight of this protocol is the regiospecific activation of less reactive benzylic C(sp 3 )−H bond as compared to heteroatom‐directed more reactive C(sp 2 )−H bond, thus providing a strategy for late−stage site−selective C(sp 3 )−H bond functionalization. The reaction proceeds under air in moderate to good yields with excellent functional groups tolerance. Abstract : Palladium(II)−catalyzed inert benzylic C(sp 3 )−H bond activation of benzylphenyl sulfides and sulfoxides has been developed that affords a series of benzaldehydes via cascade C(sp 3 )−S bond cleavage in one pot under a mutual conditions. This provides a strategy for late–stage site–selective C(sp 3 )–H bond functionalization via regiospecific activation of less reactive benzylic C(sp 3 )–H bond as compared to heteroatom–directed more reactive C(sp 2 )–H bond. The catalyst is recycled under aerobic condition.