Reductive cyclization of halo-ketones to form 3-hydroxy-2-oxindoles via palladium catalyzed hydrogenation: a hydrogen-mediated Grignard addition

Inji Shin; Stephen D. Ramgren; Michael J. Krische

doi:10.1016/j.tet.2015.05.085

Reductive cyclization of halo-ketones to form 3-hydroxy-2-oxindoles via palladium catalyzed hydrogenation: a hydrogen-mediated Grignard addition

Inji Shin, Stephen D. Ramgren, Michael J. Krische

Dept. of Fine Chemistry

University of Texas at Austin

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

30 Scopus citations

Abstract

Abstract The reductive cyclization of N-oxoacyl ortho-bromoanilides to form 3-hydroxy-2-oxindoles under the conditions of palladium catalyzed hydrogenation is described. This work may be viewed as a prelude to intermolecular hydrogen-mediated Grignard-type reductive couplings of organic halides with carbonyl compounds.

Original language	English
Article number	26803
Pages (from-to)	5776-5780
Number of pages	5
Journal	Tetrahedron
Volume	71
Issue number	35
DOIs	https://doi.org/10.1016/j.tet.2015.05.085
State	Published - 25 Jul 2015

Keywords

Carbonyl addition
Hydrogenation
Hydroxyl oxindole
Palladium
Reductive coupling

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10.1016/j.tet.2015.05.085

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title = "Reductive cyclization of halo-ketones to form 3-hydroxy-2-oxindoles via palladium catalyzed hydrogenation: a hydrogen-mediated Grignard addition",

abstract = "Abstract The reductive cyclization of N-oxoacyl ortho-bromoanilides to form 3-hydroxy-2-oxindoles under the conditions of palladium catalyzed hydrogenation is described. This work may be viewed as a prelude to intermolecular hydrogen-mediated Grignard-type reductive couplings of organic halides with carbonyl compounds.",

keywords = "Carbonyl addition, Hydrogenation, Hydroxyl oxindole, Palladium, Reductive coupling",

author = "Inji Shin and Ramgren, {Stephen D.} and Krische, {Michael J.}",

note = "Publisher Copyright: {\textcopyright} 2015 Elsevier Ltd.",

year = "2015",

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day = "25",

doi = "10.1016/j.tet.2015.05.085",

language = "English",

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journal = "Tetrahedron",

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T1 - Reductive cyclization of halo-ketones to form 3-hydroxy-2-oxindoles via palladium catalyzed hydrogenation

T2 - a hydrogen-mediated Grignard addition

AU - Shin, Inji

AU - Ramgren, Stephen D.

AU - Krische, Michael J.

PY - 2015/7/25

Y1 - 2015/7/25

N2 - Abstract The reductive cyclization of N-oxoacyl ortho-bromoanilides to form 3-hydroxy-2-oxindoles under the conditions of palladium catalyzed hydrogenation is described. This work may be viewed as a prelude to intermolecular hydrogen-mediated Grignard-type reductive couplings of organic halides with carbonyl compounds.

AB - Abstract The reductive cyclization of N-oxoacyl ortho-bromoanilides to form 3-hydroxy-2-oxindoles under the conditions of palladium catalyzed hydrogenation is described. This work may be viewed as a prelude to intermolecular hydrogen-mediated Grignard-type reductive couplings of organic halides with carbonyl compounds.

KW - Carbonyl addition

KW - Hydrogenation

KW - Hydroxyl oxindole

KW - Palladium

KW - Reductive coupling

UR - http://www.scopus.com/inward/record.url?scp=84937814848&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2015.05.085

DO - 10.1016/j.tet.2015.05.085

M3 - Article

AN - SCOPUS:84937814848

SN - 0040-4020

VL - 71

SP - 5776

EP - 5780

JO - Tetrahedron

JF - Tetrahedron

IS - 35

M1 - 26803

ER -

Reductive cyclization of halo-ketones to form 3-hydroxy-2-oxindoles via palladium catalyzed hydrogenation: a hydrogen-mediated Grignard addition

Abstract

Keywords

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