Redox-Neutral Ruthenium(II)-Catalyzed Enol-Directed Arene C-H Alkylation with Maleimides

Sudeshna Mondal; Ratnadeep Bera; Deepan Chowdhury; Suman Dana; Mahiuddin Baidya

doi:10.1021/acs.orglett.2c03858

Redox-Neutral Ruthenium(II)-Catalyzed Enol-Directed Arene C-H Alkylation with Maleimides

Sudeshna Mondal, Ratnadeep Bera, Deepan Chowdhury, Suman Dana, Mahiuddin Baidya

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

8 Scopus citations

Abstract

An enol-assisted regioselective arene C-H alkylation with maleimides is developed under redox-neutral ruthenium(II) catalysis, offering a wide variety of valuable 3-aryl succinimides including amino acid embedded frameworks in good to excellent yields. The products were also aromatized to produce synthetically useful resorcinol-based biaryls. Mechanistic studies support an organometallic pathway with a reversible C-H metalation step for this reaction.

Original language	English
Pages (from-to)	70-75
Number of pages	6
Journal	Organic Letters
Volume	25
Issue number	1
DOIs	https://doi.org/10.1021/acs.orglett.2c03858
State	Published - 13 Jan 2023
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Redox-Neutral Ruthenium(II)-Catalyzed Enol-Directed Arene C-H Alkylation with Maleimides",

abstract = "An enol-assisted regioselective arene C-H alkylation with maleimides is developed under redox-neutral ruthenium(II) catalysis, offering a wide variety of valuable 3-aryl succinimides including amino acid embedded frameworks in good to excellent yields. The products were also aromatized to produce synthetically useful resorcinol-based biaryls. Mechanistic studies support an organometallic pathway with a reversible C-H metalation step for this reaction.",

author = "Sudeshna Mondal and Ratnadeep Bera and Deepan Chowdhury and Suman Dana and Mahiuddin Baidya",

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AU - Mondal, Sudeshna

AU - Bera, Ratnadeep

AU - Chowdhury, Deepan

AU - Dana, Suman

AU - Baidya, Mahiuddin

PY - 2023/1/13

Y1 - 2023/1/13

N2 - An enol-assisted regioselective arene C-H alkylation with maleimides is developed under redox-neutral ruthenium(II) catalysis, offering a wide variety of valuable 3-aryl succinimides including amino acid embedded frameworks in good to excellent yields. The products were also aromatized to produce synthetically useful resorcinol-based biaryls. Mechanistic studies support an organometallic pathway with a reversible C-H metalation step for this reaction.

AB - An enol-assisted regioselective arene C-H alkylation with maleimides is developed under redox-neutral ruthenium(II) catalysis, offering a wide variety of valuable 3-aryl succinimides including amino acid embedded frameworks in good to excellent yields. The products were also aromatized to produce synthetically useful resorcinol-based biaryls. Mechanistic studies support an organometallic pathway with a reversible C-H metalation step for this reaction.

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Redox-Neutral Ruthenium(II)-Catalyzed Enol-Directed Arene C-H Alkylation with Maleimides

Abstract

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