Iridium(III)-Catalyzed Selective and Mild C-H Amidation of Cyclic N-Sulfonyl Ketimines with Organic Azides

Manikantha Maraswami; Gang Chen; Teck Peng Loh

doi:10.1002/adsc.201700785

Iridium(III)-Catalyzed Selective and Mild C-H Amidation of Cyclic N-Sulfonyl Ketimines with Organic Azides

Manikantha Maraswami, Gang Chen^*, Teck Peng Loh

^*Corresponding author for this work

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

22 Citations (Scopus)

Abstract

A general protocol for iridium catalyzed direct C−H amidation of cyclic N-sulfonyl ketimines using sulfonyl, acyl and aryl azides as nitrogen source is reported herein. The reaction takes place at room temperature with acyl and aryl azides, while an elevated temperature needed with sulfonyl azides to furnish aminated sultams in excellent yields with complete chemo and regioselectivity, thus providing a robust and environmentally benign process to the synthesis of aminosultams. (Figure presented.).

Original language	English
Pages (from-to)	416-421
Number of pages	6
Journal	Advanced Synthesis and Catalysis
Volume	360
Issue number	3
DOIs	https://doi.org/10.1002/adsc.201700785
Publication status	Published - Feb 1 2018
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

ASJC Scopus Subject Areas

Catalysis
Organic Chemistry

Keywords

Amidation
azides
C−H activation
Iridium
sultams

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10.1002/adsc.201700785

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title = "Iridium(III)-Catalyzed Selective and Mild C-H Amidation of Cyclic N-Sulfonyl Ketimines with Organic Azides",

abstract = "A general protocol for iridium catalyzed direct C−H amidation of cyclic N-sulfonyl ketimines using sulfonyl, acyl and aryl azides as nitrogen source is reported herein. The reaction takes place at room temperature with acyl and aryl azides, while an elevated temperature needed with sulfonyl azides to furnish aminated sultams in excellent yields with complete chemo and regioselectivity, thus providing a robust and environmentally benign process to the synthesis of aminosultams. (Figure presented.).",

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AU - Maraswami, Manikantha

AU - Chen, Gang

AU - Loh, Teck Peng

PY - 2018/2/1

Y1 - 2018/2/1

N2 - A general protocol for iridium catalyzed direct C−H amidation of cyclic N-sulfonyl ketimines using sulfonyl, acyl and aryl azides as nitrogen source is reported herein. The reaction takes place at room temperature with acyl and aryl azides, while an elevated temperature needed with sulfonyl azides to furnish aminated sultams in excellent yields with complete chemo and regioselectivity, thus providing a robust and environmentally benign process to the synthesis of aminosultams. (Figure presented.).

AB - A general protocol for iridium catalyzed direct C−H amidation of cyclic N-sulfonyl ketimines using sulfonyl, acyl and aryl azides as nitrogen source is reported herein. The reaction takes place at room temperature with acyl and aryl azides, while an elevated temperature needed with sulfonyl azides to furnish aminated sultams in excellent yields with complete chemo and regioselectivity, thus providing a robust and environmentally benign process to the synthesis of aminosultams. (Figure presented.).

KW - Amidation

KW - azides

KW - C−H activation

KW - Iridium

KW - sultams

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Iridium(III)-Catalyzed Selective and Mild C-H Amidation of Cyclic N-Sulfonyl Ketimines with Organic Azides

Abstract

Bibliographical note

ASJC Scopus Subject Areas

Keywords

Access to Document

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