Phenyliodine diacetate oxidation with

Environmentally benign oxidation of sulfides to sulfoxides was reported by Kita and co-workers by using iodine(III) reagents such as iodosobenzene (PhIO) or phenyliodine diacetate (PIDA) with KBr in water. 

Li X-Q, Wang W-K, Han Y-X, Zhang C (2010) One-pot synthesis of symmetrical 1,3-diarylureas ot substituted benzamides directly from benzylic primary alcohols and effective oxidation of secondary alcohols to ketones using phenyliodine diacetate in combination with sodium azide. Adv Synth Catal 352(14-15) 2588-2598... 

Method A represents a one-pot synthesis of NSBVs 45 (Scheme 24). Reactimi of 1 with 2.4 equiv of nitrile readily afforded the dianion 43 [63]. Addition of di-tert-butyl peroxide ((f-BuO)2, 4.0 equiv) as oxidant led to l,5-bridged-2,6-diazasemi-bullvalenes 45a-45f with different substituents at 3,7-position (Type 1, Type 11) in moderate yields [70]. Method B represents a stepwise synthesis of NSBV 45 (Scheme 24). The dianions 43 could be readily in situ generated via di-lithiation of A -bipyrrolines 44. Sequential addition of phenyliodine diacetate (Phl(OAc)2) as oxidant afforded their corresponding NSBVs 45 in good isolated yields. For the synthesis of Type 1 NSBV derivatives. Method B was found to be more efficient than Method A. 1,5-Dialkyl substituted A -bipyrroUnes 44 could also be converted to their corresponding non-bridged NSBVs 45g and 45h (Type 111) in 72% and 73% isolated yield, respectively [70]. 

Yan, M., Chen, Z., and Zheng, Q. (2003). Organic reactions in ionic liquids oxidative dimerisation of thioamides with phenyliodine(lll) diacetate. /. Chem. Res. (S), 618-619. 

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