Cascade Amination and Acetone Monoarylation with Aryl Iodides by Palladium/Norbornene Cooperative Catalysis

Wai Chung Fu; Bin Zheng; Qingyang Zhao; Wesley Ting Kwok Chan; Fuk Yee Kwong

doi:10.1021/acs.orglett.7b02023

Cascade Amination and Acetone Monoarylation with Aryl Iodides by Palladium/Norbornene Cooperative Catalysis

Wai Chung Fu, Bin Zheng, Qingyang Zhao, Wesley Ting Kwok Chan, Fuk Yee Kwong

Department of Applied Biology and Chemical Technology

Research output: Journal article publication › Journal article › Academic research › peer-review

37 Citations (Scopus)

Abstract

A palladium/norbornene cocatalyzed three-component reaction of aryl iodides, O-benzoylhydroxylamines, and acetone is reported. o′-Aminoaryl acetones or o,o′-diaminoaryl acetones are efficiently prepared via tandem ortho-C-H amination/ipso-C-I α-arylation sequence, and the regiospecificity has been confirmed by X-ray analysis. The proposed method addresses the condensation/amination of free-N-H-bearing substrates in acetone monoarylations and the synthesis of extremely congested 2,6-disubstituted aryl acetones.

Original language	English
Pages (from-to)	4335-4338
Number of pages	4
Journal	Organic Letters
Volume	19
Issue number	16
DOIs	https://doi.org/10.1021/acs.orglett.7b02023
Publication status	Published - 18 Aug 2017

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

More information

10.1021/acs.orglett.7b02023

http://hdl.handle.net/10397/95305

Cite this

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title = "Cascade Amination and Acetone Monoarylation with Aryl Iodides by Palladium/Norbornene Cooperative Catalysis",

abstract = "A palladium/norbornene cocatalyzed three-component reaction of aryl iodides, O-benzoylhydroxylamines, and acetone is reported. o′-Aminoaryl acetones or o,o′-diaminoaryl acetones are efficiently prepared via tandem ortho-C-H amination/ipso-C-I α-arylation sequence, and the regiospecificity has been confirmed by X-ray analysis. The proposed method addresses the condensation/amination of free-N-H-bearing substrates in acetone monoarylations and the synthesis of extremely congested 2,6-disubstituted aryl acetones.",

author = "Fu, {Wai Chung} and Bin Zheng and Qingyang Zhao and Chan, {Wesley Ting Kwok} and Kwong, {Fuk Yee}",

note = "Funding Information: We thank RGC of Hong Kong (GRF: 153367/16P; CRF: C5023-14G; and PolyU11/CRF/13E [X-ray equipment]) for financial support. National Natural Science Foundation of China (Grant No. 21602172) is gratefully acknowledged. Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

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doi = "10.1021/acs.orglett.7b02023",

language = "English",

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AU - Fu, Wai Chung

AU - Zheng, Bin

AU - Zhao, Qingyang

AU - Chan, Wesley Ting Kwok

AU - Kwong, Fuk Yee

N1 - Funding Information: We thank RGC of Hong Kong (GRF: 153367/16P; CRF: C5023-14G; and PolyU11/CRF/13E [X-ray equipment]) for financial support. National Natural Science Foundation of China (Grant No. 21602172) is gratefully acknowledged. Publisher Copyright: © 2017 American Chemical Society.

PY - 2017/8/18

Y1 - 2017/8/18

N2 - A palladium/norbornene cocatalyzed three-component reaction of aryl iodides, O-benzoylhydroxylamines, and acetone is reported. o′-Aminoaryl acetones or o,o′-diaminoaryl acetones are efficiently prepared via tandem ortho-C-H amination/ipso-C-I α-arylation sequence, and the regiospecificity has been confirmed by X-ray analysis. The proposed method addresses the condensation/amination of free-N-H-bearing substrates in acetone monoarylations and the synthesis of extremely congested 2,6-disubstituted aryl acetones.

AB - A palladium/norbornene cocatalyzed three-component reaction of aryl iodides, O-benzoylhydroxylamines, and acetone is reported. o′-Aminoaryl acetones or o,o′-diaminoaryl acetones are efficiently prepared via tandem ortho-C-H amination/ipso-C-I α-arylation sequence, and the regiospecificity has been confirmed by X-ray analysis. The proposed method addresses the condensation/amination of free-N-H-bearing substrates in acetone monoarylations and the synthesis of extremely congested 2,6-disubstituted aryl acetones.

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U2 - 10.1021/acs.orglett.7b02023

DO - 10.1021/acs.orglett.7b02023

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Cascade Amination and Acetone Monoarylation with Aryl Iodides by Palladium/Norbornene Cooperative Catalysis

Abstract

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