Phenyliodine diacetate

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. 

The oxidative fluorination of 4-alkylphenols to give the 4-fluoro-4-alkylcyclohexa-2,5-dien-l-ones can be achieved by using hypervalent iodine reagents, such as phenyliodo bis(trifluoroacetate) or phenyliodine diacetate in the presence of pyridinium polyhydrogen fluoride (equation 81) vide infra). ... 

R" = CH3, OCH3, OEt, OBn, Ph, 4-MeOCeH4 PIDA = phenyliodine dIacetate Scheme 42... 

Phenyliodine diacetate-mediated oxidative cleavage of cyclobutanols leads to the formation of y-hydroxy ketones, y-Substituted y-hydroxy ketones were obtained from 2-substituted cyclobutanols through regioselective C-C bond cleavage. ... 

An interesting application of phenyliodine diacetate is the reaction with carbon acids such as / -diketones under mild, basic conditions to yield iodonium ylides (EWG = electron-withdrawing group) ... 

Takeda et al. applied a hypervalent iodine(III)-initiated oxidative [4 + 2] cyclization of o-phenylenediamines and electron-poor alkynes to the preparation of quinoxalines 125 from alkyne starting materials without the presence of metal catalysts (Scheme 52) (13CC9266). Optimal reaction conditions were found to be phenyliodine diacetate (PIDA) (2 equiv) as the... 

R. Cheng, T. Guo, D. Zhang-Negrerie, Y. Du, K. Zhao, One-pot synthesis of quinazolinones from anthranilamides and aldehydes via p-toluenesulfonic acid catalyzed cyclocondensation and phenyliodine diacetate mediated oxidative dehydrogenation. Synthesis 45 (2013) 2998-3006. 

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... 

Phenyliodine diacetate Phenyl isocyanate 2.Phenyl-1W-isoindole 1,3(2/ -dione... 

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]. 

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