Oxidative Route to Indoles via Intramolecular Amino-Hydroxylation of o-Allenyl Anilines

Nicholas R. Lauta; Ryan E. Williams; David T. Smith; Vlad K. Kumirov; Jon T. Njardarson

doi:10.1021/acs.joc.1c01379

Oxidative Route to Indoles via Intramolecular Amino-Hydroxylation of o-Allenyl Anilines

Nicholas R. Lauta
, Ryan E. Williams
, David T. Smith
, Vlad K. Kumirov
, Jon T. Njardarson

Research output: Contribution to journal › Article › peer-review

3 Scopus citations

Abstract

A new intramolecular oxidative amino-hydroxylation of o-allenyl anilines is reported. Treatment of carbamate-protected anilines with lead(IV) carboxylates in dichloromethane at room temperature results in facile tandem C-N (allene cyclization) and C-O bond formation (carboxylate trapping) to form indole products. Detailed reaction scope, mechanistic and kinetic studies suggest a reaction pathway involving an initial Wessely dearomatization step followed by cyclization and rearomatization.

Original language	English (US)
Pages (from-to)	10713-10723
Number of pages	11
Journal	Journal of Organic Chemistry
Volume	86
Issue number	15
DOIs	https://doi.org/10.1021/acs.joc.1c01379
State	Published - Aug 6 2021
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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10.1021/acs.joc.1c01379

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title = "Oxidative Route to Indoles via Intramolecular Amino-Hydroxylation of o-Allenyl Anilines",

abstract = "A new intramolecular oxidative amino-hydroxylation of o-allenyl anilines is reported. Treatment of carbamate-protected anilines with lead(IV) carboxylates in dichloromethane at room temperature results in facile tandem C-N (allene cyclization) and C-O bond formation (carboxylate trapping) to form indole products. Detailed reaction scope, mechanistic and kinetic studies suggest a reaction pathway involving an initial Wessely dearomatization step followed by cyclization and rearomatization.",

author = "Lauta, \{Nicholas R.\} and Williams, \{Ryan E.\} and Smith, \{David T.\} and Kumirov, \{Vlad K.\} and Njardarson, \{Jon T.\}",

note = "Publisher Copyright: {\textcopyright} 2021 American Chemical Society.",

year = "2021",

month = aug,

day = "6",

doi = "10.1021/acs.joc.1c01379",

language = "English (US)",

volume = "86",

pages = "10713--10723",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "15",

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TY - JOUR

T1 - Oxidative Route to Indoles via Intramolecular Amino-Hydroxylation of o-Allenyl Anilines

AU - Lauta, Nicholas R.

AU - Williams, Ryan E.

AU - Smith, David T.

AU - Kumirov, Vlad K.

AU - Njardarson, Jon T.

PY - 2021/8/6

Y1 - 2021/8/6

N2 - A new intramolecular oxidative amino-hydroxylation of o-allenyl anilines is reported. Treatment of carbamate-protected anilines with lead(IV) carboxylates in dichloromethane at room temperature results in facile tandem C-N (allene cyclization) and C-O bond formation (carboxylate trapping) to form indole products. Detailed reaction scope, mechanistic and kinetic studies suggest a reaction pathway involving an initial Wessely dearomatization step followed by cyclization and rearomatization.

AB - A new intramolecular oxidative amino-hydroxylation of o-allenyl anilines is reported. Treatment of carbamate-protected anilines with lead(IV) carboxylates in dichloromethane at room temperature results in facile tandem C-N (allene cyclization) and C-O bond formation (carboxylate trapping) to form indole products. Detailed reaction scope, mechanistic and kinetic studies suggest a reaction pathway involving an initial Wessely dearomatization step followed by cyclization and rearomatization.

UR - https://www.scopus.com/pages/publications/85111172973

UR - https://www.scopus.com/pages/publications/85111172973#tab=citedBy

U2 - 10.1021/acs.joc.1c01379

DO - 10.1021/acs.joc.1c01379

M3 - Article

AN - SCOPUS:85111172973

SN - 0022-3263

VL - 86

SP - 10713

EP - 10723

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 15

ER -

Oxidative Route to Indoles via Intramolecular Amino-Hydroxylation of o-Allenyl Anilines

Abstract

ASJC Scopus subject areas

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CCDC 2087886: Experimental Crystal Structure Determination

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Oxidative Route to Indoles via Intramolecular Amino-Hydroxylation of o-Allenyl Anilines

Abstract

ASJC Scopus subject areas

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Datasets

CCDC 2087886: Experimental Crystal Structure Determination

Cite this