Sulfoximine Assisted Pd(II)-Catalyzed Bromination and Chlorination of Primary β‑C(sp3)–H Bond

Sulfoximine Assisted Pd(II)-Catalyzed Bromination and Chlorination of Primary β‑C(sp3)–H Bond

S-Methyl-S-2-pyridyl-sulfoximine (MPyS) directed bromination and chlorination of the 1°-β-C­(sp3)–H bond of MPyS-N-amides is realized under the influence of N-Br/Cl-phthalimides and a Pd­(II)-catalyst. The sequential halogenation and acetoxylation of α-dimethyl MPyS-N-amides constructs highly functi...

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Veröffentlicht in:Organic letters 2014-10, Vol.16 (20), p.5258-5261
Hauptverfasser: Rit, Raja K, Yadav, M. Ramu, Ghosh, Koushik, Shankar, Majji, Sahoo, Akhila K
Format: Artikel
Sprache:eng
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Zusammenfassung:S-Methyl-S-2-pyridyl-sulfoximine (MPyS) directed bromination and chlorination of the 1°-β-C­(sp3)–H bond of MPyS-N-amides is realized under the influence of N-Br/Cl-phthalimides and a Pd­(II)-catalyst. The sequential halogenation and acetoxylation of α-dimethyl MPyS-N-amides constructs highly functionalized α-trisubstituted aliphatic acid derivatives. The MPyS directing group is cleaved from the halogenated products and recovered.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol502337b