Direct synthesis of phthalimides <i>via</i> palladium-catalysed double carbonylation of <i>o</i>-dihaloarenes with nitroarenes

Liu, Chenwei; An, Tongshun; Yuan, Weiheng; Dai, Huiying; Liang, Xiaolan; Yin, Zhiping

doi:10.1039/d3cc04126c

Chem. Commun.

2023

DOI: 10.1039/d3cc04126c

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Direct synthesis of phthalimides via palladium-catalysed double carbonylation of o-dihaloarenes with nitroarenes

Chenwei Liu,

Tongshun An,

Weiheng Yuan

et al.

Abstract: A novel carbonylation of nitroarenes with o-dihaloarenes was developed to construct various N-substituted phthalimides. Key to the success of this transformation is the use of Mo(CO)6 which serves as both reducing agents and carbonyl sources.

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Molybdenum‐Catalyzed One‐Pot Multi‐Step Synthesis of N‐Polyheterocycles from Nitroarenes and Glycols

Gómez‐Gil,

Cases,

Hernández‐Ruiz

et al. 2024

Eur J Org Chem

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We report the efficient, sustainable one‐pot synthesis of a wide variety of N‐polyheterocycles, such as imidazo‐quinolines and quinoxalines, and furoquinolines, from easily available nitroaromatics and glycols via a molybdenum catalytic domino reduction‐imine formation‐intramolecular cyclization‐oxidation sequence. It is worth highlighting that the recycling and incorporation of the waste carbonyl byproduct, generated in the reduction step, into the final compound is realized. In addition, the overall efficiency and atom economy of the process are further improved owing to the participation of one reaction intermediate as reductant that allows lowering the amount of external reducing agent employed.

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Molybdenum‐Catalyzed One‐Pot Multi‐Step Synthesis of N‐Polyheterocycles from Nitroarenes and Glycols

Gómez‐Gil,

Cases,

Hernández‐Ruiz

et al. 2024

Eur J Org Chem

View full text Add to dashboard Cite

show abstract

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Direct synthesis of phthalimides via palladium-catalysed double carbonylation of o-dihaloarenes with nitroarenes

Abstract: A novel carbonylation of nitroarenes with o-dihaloarenes was developed to construct various N-substituted phthalimides. Key to the success of this transformation is the use of Mo(CO)6 which serves as both reducing agents and carbonyl sources.

Cited by 1 publication

References 54 publications

Molybdenum‐Catalyzed One‐Pot Multi‐Step Synthesis of N‐Polyheterocycles from Nitroarenes and Glycols

Molybdenum‐Catalyzed One‐Pot Multi‐Step Synthesis of N‐Polyheterocycles from Nitroarenes and Glycols

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