Single-step construction of an acetoxypyrroloindole skeleton <i>via</i> tandem iodocyclization/acetoxylation of indoles

Kimishima, Atsushi; Kato, Hiroki; Nakaguro, Keijin; Arai, Masayoshi

doi:10.1039/d2ob01001a

Cited by 2 publications

(2 citation statements)

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“…Using Pd(II)/Al 2 O 3 catalysis of oxo-benzoxazine derivatives, a novel solvent-free direct sp 2 CÀ H bond functionalization (oxygenation) approach was reported by Prajapati and co-workers (79!80) (Scheme 26). [106] The optimized reaction parameters are:PIDA (1.1 equiv. ), Pd(OAc) 2 (1 mol %), Al 2 O 3 (0.5 equiv.)…”

Section: Acetoxylation/acetalization/alkoxylationmentioning

confidence: 99%

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Applications of Phenyliodine(III)diacetate in C−H Functionalization and Hetero‐Hetero Bond Formations: A Septennial Update

et al. 2023

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One of the most widely utilized hypervalent iodines used as an oxidizing agent in organic chemistry is (diacetoxyiodo)benzene (PhI(OAc)2), also known as (DAIB), phenyliodine(III) diacetate (PIDA). In this review, authors have comprehensively and systematically presented the various applications of PIDA in organic synthesis involving C−C, C‐hetero, hetero‐hetero and multiple bond forms from the summer of 2015 to the present. The role of PIDA was also emphasized for the success of particular organic transformation. Recent literature has produced a substantial number of publications (∼100), and this septennial review examines all of the most recent breakthroughs in the field of study.

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Section: Acetoxylation/acetalization/alkoxylationmentioning

confidence: 99%

“…Using Pd(II)/Al 2 O 3 catalysis of oxo‐benzoxazine derivatives, a novel solvent‐free direct sp 2 C−H bond functionalization (oxygenation) approach was reported by Prajapati and co‐workers ( 79 → 80 ) (Scheme 26). [106] …”

Section: Applications Of Phenyliodine(iii)diacetatementioning

confidence: 99%

Applications of Phenyliodine(III)diacetate in C−H Functionalization and Hetero‐Hetero Bond Formations: A Septennial Update

et al. 2023

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SO₂ClF‐Promoted Chlorooxidation of Tryptamine Derivatives: Synthesis of 3,3‐Disubstituted Oxindoles

Zheng,

Lu,

et al. 2023

Asian J Org Chem

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A series of tryptamine derivatives were transformed into their corresponding 3‐chloro‐2‐oxidation products under simple and mild conditions. This protocol is an operationally simple system that utilizes a single reagent SO2ClF plays a dual role as both oxidant and chloride source and enables the construction of various 3,3‐disubstituted oxindoles with good functional group tolerance. The transformations of the product highlight its potential synthetic applications.

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Single-step construction of an acetoxypyrroloindole skeleton via tandem iodocyclization/acetoxylation of indoles

Abstract: A new single-step approach to a C3a acetoxy pyrroloindole from various indoles under hypervalent iodine and ammonium salt-mediated mild reaction conditions was developed. The described method enables the short-step synthesis of (−)-protubonine B.

Cited by 2 publications

References 22 publications

Applications of Phenyliodine(III)diacetate in C−H Functionalization and Hetero‐Hetero Bond Formations: A Septennial Update

Applications of Phenyliodine(III)diacetate in C−H Functionalization and Hetero‐Hetero Bond Formations: A Septennial Update

SO₂ClF‐Promoted Chlorooxidation of Tryptamine Derivatives: Synthesis of 3,3‐Disubstituted Oxindoles

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Single-step construction of an acetoxypyrroloindole skeleton via tandem iodocyclization/acetoxylation of indoles

Abstract: A new single-step approach to a C3a acetoxy pyrroloindole from various indoles under hypervalent iodine and ammonium salt-mediated mild reaction conditions was developed. The described method enables the short-step synthesis of (−)-protubonine B.

Cited by 2 publications

References 22 publications

Applications of Phenyliodine(III)diacetate in C−H Functionalization and Hetero‐Hetero Bond Formations: A Septennial Update

Applications of Phenyliodine(III)diacetate in C−H Functionalization and Hetero‐Hetero Bond Formations: A Septennial Update

SO2ClF‐Promoted Chlorooxidation of Tryptamine Derivatives: Synthesis of 3,3‐Disubstituted Oxindoles

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SO₂ClF‐Promoted Chlorooxidation of Tryptamine Derivatives: Synthesis of 3,3‐Disubstituted Oxindoles