Copper-catalyzed N-arylation of tert-butyl N-sulfonylcarbamates with diaryliodonium salts at room temperature

Soo Yeon Moon; Moonjee Koh; Kris Rathwell; Seo Hee Jung; Won Suk Kim

doi:10.1016/j.tet.2015.01.032

Copper-catalyzed N-arylation of tert-butyl N-sulfonylcarbamates with diaryliodonium salts at room temperature

Soo Yeon Moon, Moonjee Koh, Kris Rathwell, Seo Hee Jung, Won Suk Kim

Department of Chemistry & Nanoscience

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

10 Scopus citations

Abstract

A new and mild synthetic approach for the synthesis of N-arylsulfonamides under copper-catalyzed conditions at room temperature has been developed. The reaction employs various tert-butyl N-sulfonylcarbamates and diaryliodonium salts to avoid potential genotoxic impurities. A one-pot coupling/Boc-deprotection sequence is also reported to provide mono N-arylsulfonamides in good to excellent yields.

Original language	English
Pages (from-to)	1566-1573
Number of pages	8
Journal	Tetrahedron
Volume	71
Issue number	10
DOIs	https://doi.org/10.1016/j.tet.2015.01.032
State	Published - 11 Mar 2015

Bibliographical note

Funding Information:
This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) ( NRF-2012R1A1A1006123 ) and the New & Renewable Energy of the Korea Institute of Energy Technology Evaluation and Planning (KETEP) grant (No. 20133030000210 ).

Publisher Copyright:
© 2015 Elsevier Ltd. All rights reserved.

Keywords

Copper catalysis
Diaryliodonium salts
Mono N-arylsulfonamides
Room temperature
tert-Butyl N-sulfonylcarbamates

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10.1016/j.tet.2015.01.032

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title = "Copper-catalyzed N-arylation of tert-butyl N-sulfonylcarbamates with diaryliodonium salts at room temperature",

abstract = "A new and mild synthetic approach for the synthesis of N-arylsulfonamides under copper-catalyzed conditions at room temperature has been developed. The reaction employs various tert-butyl N-sulfonylcarbamates and diaryliodonium salts to avoid potential genotoxic impurities. A one-pot coupling/Boc-deprotection sequence is also reported to provide mono N-arylsulfonamides in good to excellent yields.",

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note = "Funding Information: This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) ( NRF-2012R1A1A1006123 ) and the New & Renewable Energy of the Korea Institute of Energy Technology Evaluation and Planning (KETEP) grant (No. 20133030000210 ). Publisher Copyright: {\textcopyright} 2015 Elsevier Ltd. All rights reserved.",

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AU - Koh, Moonjee

AU - Rathwell, Kris

AU - Jung, Seo Hee

AU - Kim, Won Suk

N1 - Funding Information: This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) ( NRF-2012R1A1A1006123 ) and the New & Renewable Energy of the Korea Institute of Energy Technology Evaluation and Planning (KETEP) grant (No. 20133030000210 ). Publisher Copyright: © 2015 Elsevier Ltd. All rights reserved.

PY - 2015/3/11

Y1 - 2015/3/11

N2 - A new and mild synthetic approach for the synthesis of N-arylsulfonamides under copper-catalyzed conditions at room temperature has been developed. The reaction employs various tert-butyl N-sulfonylcarbamates and diaryliodonium salts to avoid potential genotoxic impurities. A one-pot coupling/Boc-deprotection sequence is also reported to provide mono N-arylsulfonamides in good to excellent yields.

AB - A new and mild synthetic approach for the synthesis of N-arylsulfonamides under copper-catalyzed conditions at room temperature has been developed. The reaction employs various tert-butyl N-sulfonylcarbamates and diaryliodonium salts to avoid potential genotoxic impurities. A one-pot coupling/Boc-deprotection sequence is also reported to provide mono N-arylsulfonamides in good to excellent yields.

KW - Copper catalysis

KW - Diaryliodonium salts

KW - Mono N-arylsulfonamides

KW - Room temperature

KW - tert-Butyl N-sulfonylcarbamates

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DO - 10.1016/j.tet.2015.01.032

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JF - Tetrahedron

IS - 10

ER -

Copper-catalyzed N-arylation of tert-butyl N-sulfonylcarbamates with diaryliodonium salts at room temperature

Abstract

Bibliographical note

Keywords

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