ChemInform Abstract: Oxidative Cleavage of C2—C3 Bond in Isatin Using (Diacetoxyiodo)benzene: A Facile Synthesis of Carbamates of Alkyl Anthranilates.

Kalbandhe, Amit H.; Kavale, Ashish C.; Thorat, Prerana B.; Karade, Nandkishor N.

doi:10.1002/chin.201630034

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“…Diphenyl diselenide was used by Karade et al to enable metal-free (diacetoxy)iodobenzene-mediated C(sp 2 )-H phenylselenation of imidazo[1,2-a]pyridines and imidazo[2,1-b]thiazoles (33) in the presence of PIDA [19]. The imidazoheterocycle phenyl selenation product (34) of this procedure demonstrated broad substrate scope, good to outstanding yields, and rapid reaction times (Scheme 5).…”

Section: C-se Bond Formationmentioning

confidence: 99%

“…Isatin can be attacked by nucleophiles at the C2 and/or C3 locations, and the chemoselectivity of these reactions depends on a number of variables, including the type of nucleophile. Karade and group reported that when isatin and N-acetyl isatin (112/114) interact with PIDA, oxidative C2-C3 bond cleavage occurs, resulting in carbamates of alkyl anthranilates (113) and alkyl 2-acetamidobenzoate (115), respectively (Scheme 20) [34]. Even after refluxing for 24 hours in methanol, molecular iodine was found to be insufficient to cause oxidative C2-C3 cleavage of isatin.…”

Section: Oxidative Cleavage Of C2-c3 Bondmentioning

confidence: 99%

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Phenyliodine(III)diacetate (PIDA): Applications in Organic Synthesis

2022

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One of the hypervalent iodines most widely used as an oxidizing agent in organic chemistry is (diacetoxyiodo)benzene (PhI(OAc)2), also known as (DAIB), phenyliodine(III) diacetate (PIDA). In this septennial mini-review, the authors have concisely and systematically presented representative applications of PIDA in organic synthesis involving C-H functionalization, hetero-hetero bond formations, heterocyclic ring construction, rearrangements or migrations and miscellaneous reactions along with their interesting mechanistic aspects starting from the summer of 2015 to the present.

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Section: C-se Bond Formationmentioning

confidence: 99%

Section: Oxidative Cleavage Of C2-c3 Bondmentioning

confidence: 99%