Ruthenium(II)-Catalyzed Ortho-C-H Alkylation of Naphthylamines with Diazo Compounds for Synthesis of 2,2-Disubstituted π-Extended 3-Oxindoles in Water

Xiaogang Wang; Jin Zhang; Yuan He; Di Chen; Chao Wang; Fangzhou Yang; Weitao Wang; Yangmin Ma; Michal Szostak

doi:10.1021/acs.orglett.0c01811

Ruthenium(II)-Catalyzed Ortho-C-H Alkylation of Naphthylamines with Diazo Compounds for Synthesis of 2,2-Disubstituted π-Extended 3-Oxindoles in Water

Xiaogang Wang, Jin Zhang, Yuan He, Di Chen, Chao Wang, Fangzhou Yang, Weitao Wang, Yangmin Ma, Michal Szostak

Rutgers Newark, Chemistry

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

29 Scopus citations

Abstract

Ruthenium(II)-catalyzed ortho-C-H alkylation of naphthylamines with diazo compounds for the synthesis of 2,2-disubstituted π-extended 3-oxindoles has been developed. The method represents the first example of C-H alkylation via carbenoid insertion in water as a sustainable solvent. The procedure includes an inexpensive ruthenium catalyst as well as aqueous media and results in the release of benign N2. The π-extended 3-oxindole products exhibit favorable antitumor properties and remarkable fluorescent properties in aqueous solution for fluorescent imaging.

Original language	English (US)
Pages (from-to)	5187-5192
Number of pages	6
Journal	Organic letters
Volume	22
Issue number	13
DOIs	https://doi.org/10.1021/acs.orglett.0c01811
State	Published - Jul 2 2020

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.0c01811

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title = "Ruthenium(II)-Catalyzed Ortho-C-H Alkylation of Naphthylamines with Diazo Compounds for Synthesis of 2,2-Disubstituted π-Extended 3-Oxindoles in Water",

abstract = "Ruthenium(II)-catalyzed ortho-C-H alkylation of naphthylamines with diazo compounds for the synthesis of 2,2-disubstituted π-extended 3-oxindoles has been developed. The method represents the first example of C-H alkylation via carbenoid insertion in water as a sustainable solvent. The procedure includes an inexpensive ruthenium catalyst as well as aqueous media and results in the release of benign N2. The π-extended 3-oxindole products exhibit favorable antitumor properties and remarkable fluorescent properties in aqueous solution for fluorescent imaging.",

author = "Xiaogang Wang and Jin Zhang and Yuan He and Di Chen and Chao Wang and Fangzhou Yang and Weitao Wang and Yangmin Ma and Michal Szostak",

note = "Funding Information: J.Z. thanks the China Scholarship Council (No. 201808610096). Support was provided by the Foundation for Young Scholars of Shaanxi University of Science and Technology (No. BJ12-26). M.S. thanks Rutgers University and the NSF (CAREER CHE-1650766). Publisher Copyright: {\textcopyright} 2020 American Chemical Society.",

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doi = "10.1021/acs.orglett.0c01811",

language = "English (US)",

volume = "22",

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journal = "Organic Letters",

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T1 - Ruthenium(II)-Catalyzed Ortho-C-H Alkylation of Naphthylamines with Diazo Compounds for Synthesis of 2,2-Disubstituted π-Extended 3-Oxindoles in Water

AU - Wang, Xiaogang

AU - Zhang, Jin

AU - He, Yuan

AU - Chen, Di

AU - Wang, Chao

AU - Yang, Fangzhou

AU - Wang, Weitao

AU - Ma, Yangmin

AU - Szostak, Michal

N1 - Funding Information: J.Z. thanks the China Scholarship Council (No. 201808610096). Support was provided by the Foundation for Young Scholars of Shaanxi University of Science and Technology (No. BJ12-26). M.S. thanks Rutgers University and the NSF (CAREER CHE-1650766). Publisher Copyright: © 2020 American Chemical Society.

PY - 2020/7/2

Y1 - 2020/7/2

N2 - Ruthenium(II)-catalyzed ortho-C-H alkylation of naphthylamines with diazo compounds for the synthesis of 2,2-disubstituted π-extended 3-oxindoles has been developed. The method represents the first example of C-H alkylation via carbenoid insertion in water as a sustainable solvent. The procedure includes an inexpensive ruthenium catalyst as well as aqueous media and results in the release of benign N2. The π-extended 3-oxindole products exhibit favorable antitumor properties and remarkable fluorescent properties in aqueous solution for fluorescent imaging.

AB - Ruthenium(II)-catalyzed ortho-C-H alkylation of naphthylamines with diazo compounds for the synthesis of 2,2-disubstituted π-extended 3-oxindoles has been developed. The method represents the first example of C-H alkylation via carbenoid insertion in water as a sustainable solvent. The procedure includes an inexpensive ruthenium catalyst as well as aqueous media and results in the release of benign N2. The π-extended 3-oxindole products exhibit favorable antitumor properties and remarkable fluorescent properties in aqueous solution for fluorescent imaging.

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Ruthenium(II)-Catalyzed Ortho-C-H Alkylation of Naphthylamines with Diazo Compounds for Synthesis of 2,2-Disubstituted π-Extended 3-Oxindoles in Water

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