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8‐Aminoquinoline‐Assisted Synthesis and Crystal Structure Studies of Ferrocenyl Aryl Sulfones
Author(s) -
Sattar Moh.,
Kumar Nitin,
Yadav Prateek,
Mandhar Yogesh,
Kumar Sangit
Publication year - 2019
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201901334
Subject(s) - ferrocene , intramolecular force , chemistry , substituent , aryl , ring (chemistry) , crystal structure , medicinal chemistry , catalysis , copper , amide , nitro , bent molecular geometry , crystallography , stereochemistry , organic chemistry , electrochemistry , alkyl , electrode
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.