Isoindolinones via Copper-Catalyzed Intramolecular Benzylic C-H Sulfamidation

Robin Bedford; John G Bowen; Carolina Méndez-Gálvez

doi:10.1021/acs.joc.6b02970

Isoindolinones via Copper-Catalyzed Intramolecular Benzylic C-H Sulfamidation

Robin Bedford, John G Bowen, Carolina Méndez-Gálvez

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Abstract

2-Benzyl-N-tosylbenzamides and related substrates undergo copper-catalyzed intramolecular sulfamidation at the ben-zylic methylene to give N-arylsuflonyl-1-arylisoindolinones, which can be N-deprotected using samarium iodide to generate the free 1-arylisoindolinones. Preliminary mechanistic studies indicate that the rate-determining step is not C-H bond cleavage, but are instead consistent with slow oxidation of a copper π-arene intermediate.

Original language	English
Pages (from-to)	1719-1725
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	82
Issue number	3
Early online date	13 Jan 2017
DOIs	https://doi.org/10.1021/acs.joc.6b02970
Publication status	Published - 3 Feb 2017

Keywords

Copper
C-H activation
amidation
sulfamidation

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This is the author accepted manuscript (AAM). The final published version (version of record) is available online via ACS at http://pubs.acs.org/doi/abs/10.1021/acs.joc.6b02970. Please refer to any applicable terms of use of the publisher.
Accepted author manuscript, 996 KBLicence: CC BY-NC

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Crosby, J.
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title = "Isoindolinones via Copper-Catalyzed Intramolecular Benzylic C-H Sulfamidation",

abstract = "2-Benzyl-N-tosylbenzamides and related substrates undergo copper-catalyzed intramolecular sulfamidation at the ben-zylic methylene to give N-arylsuflonyl-1-arylisoindolinones, which can be N-deprotected using samarium iodide to generate the free 1-arylisoindolinones. Preliminary mechanistic studies indicate that the rate-determining step is not C-H bond cleavage, but are instead consistent with slow oxidation of a copper π-arene intermediate.",

keywords = "Copper, C-H activation, amidation, sulfamidation",

author = "Robin Bedford and Bowen, {John G} and Carolina M{\'e}ndez-G{\'a}lvez",

year = "2017",

month = feb,

day = "3",

doi = "10.1021/acs.joc.6b02970",

language = "English",

volume = "82",

pages = "1719--1725",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "3",

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TY - JOUR

T1 - Isoindolinones via Copper-Catalyzed Intramolecular Benzylic C-H Sulfamidation

AU - Bedford, Robin

AU - Bowen, John G

AU - Méndez-Gálvez, Carolina

PY - 2017/2/3

Y1 - 2017/2/3

N2 - 2-Benzyl-N-tosylbenzamides and related substrates undergo copper-catalyzed intramolecular sulfamidation at the ben-zylic methylene to give N-arylsuflonyl-1-arylisoindolinones, which can be N-deprotected using samarium iodide to generate the free 1-arylisoindolinones. Preliminary mechanistic studies indicate that the rate-determining step is not C-H bond cleavage, but are instead consistent with slow oxidation of a copper π-arene intermediate.

AB - 2-Benzyl-N-tosylbenzamides and related substrates undergo copper-catalyzed intramolecular sulfamidation at the ben-zylic methylene to give N-arylsuflonyl-1-arylisoindolinones, which can be N-deprotected using samarium iodide to generate the free 1-arylisoindolinones. Preliminary mechanistic studies indicate that the rate-determining step is not C-H bond cleavage, but are instead consistent with slow oxidation of a copper π-arene intermediate.

KW - Copper

KW - C-H activation

KW - amidation

KW - sulfamidation

U2 - 10.1021/acs.joc.6b02970

DO - 10.1021/acs.joc.6b02970

M3 - Article (Academic Journal)

C2 - 28084074

VL - 82

SP - 1719

EP - 1725

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 3

ER -

Isoindolinones via Copper-Catalyzed Intramolecular Benzylic C-H Sulfamidation

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Keywords

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