8‐Aminoquinoline‐Assisted Synthesis and Crystal Structure Studies of Ferrocenyl Aryl Sulfones. Issue 24 (28th November 2019)

• Record Type: Journal Article
• Authors: Sattar, Moh.; Kumar, Nitin; Yadav, Prateek; Mandhar, Yogesh; Kumar, Sangit
• Is Part Of: Chemistry, an Asian journal. Volume 14:Issue 24(2019)
• Page Start: 4807
• Page End: 4813
• Publication Date: 2019-11-28
• Subjects: 8-aminoquinoline -- C−H functionalization -- copper catalysis -- directing group -- ferrocene -- sodium sulfinates; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/asia.201901334
• Languages: English
• ISSNs: 1861-4728

Abstract

Abstract: A copper‐catalyzed 8‐aminoquinoline‐directed oxidative cross‐coupling of the C−H bond of ferrocene with sodium arylsulfinates has been achieved. The robust copper catalyst tolerates a range of methyl, tert ‐butyl, bromo, chloro, iodo and nitro functional groups in the phenyl ring, and set the stage for the synthesis of substituted ferrocene sulfones. Furthermore, X‐ray crystal structure study on several ferrocenyl sulfones reveals the tetrahedral geometry around sulfur; interestingly, the O‐S‐O angle is larger than the electropositive substituent C‐S‐C angle which could be explained by Bent's rule. Further, unusual intramolecular O(S)⋅⋅⋅N(amide) short contacts (2.925–3) and O(S)⋅⋅⋅C=O were also noticed in ferrocenyl sulfones. Abstract : Arylsulfonation in ferrocene has been achieved by a copper‐catalyzed 8‐aminoquinoline‐directed oxidative cross‐coupling reaction using sodium arylsulfinates. Single X‐ray crystal structure studies on several ferrocenyl sulfones reveal the tetrahedral geometry around sulfur; interestingly, the O‐S‐O angle is larger than that of the electropositive substituent C‐S‐C which could be explained by Bent's rule.