Revealing the electron driven mechanism in metal catalyzed Kumada cross coupling reaction.

Noriyuki Takai, Takuro Tsutsumi, Kenichiro Saita, Tetsuya Taketsugu, Takao Tsuneda

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Article in Scientific reports, 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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5 · Who and what money

Authors and funding

5 authors.

Noriyuki TakaiGraduate School of Chemical Sciences and Engineering, Hokkaido University, Sapporo, 060-8628, Japan.

Takuro TsutsumiDepartment of Chemistry, Faculty of Science, Hokkaido University, Sapporo, 060-0810, Japan.

Kenichiro SaitaDepartment of Chemistry, Faculty of Science, Hokkaido University, Sapporo, 060-0810, Japan.

Tetsuya TaketsuguDepartment of Chemistry, Faculty of Science, Hokkaido University, Sapporo, 060-0810, Japan.

Takao TsunedaDepartment of Chemistry, Faculty of Science, Hokkaido University, Sapporo, 060-0810, Japan. takaotsuneda@sci.hokudai.ac.jp.

Funding

Core Research for Evolutional Science and Technology JPMJCR1902

6 · The paper itself

Abstract

The electron motion mechanism of the metal-catalyzed Kumada cross-coupling reaction, which synthesizes biphenyl from chlorobenzene and phenylmagnesium chloride (a Grignard reagent) using a palladium (Pd) complex with an auxiliary phosphine ligand, is elucidated. This analysis is grounded in reactive orbital energy theory (ROET), enabling the examination of electron motions in comprehensive chemical reactions. We first calculated the intrinsic reaction coordinates (IRCs) for the four key processes of this reaction: oxidative addition, transmetalation steps 1 and 2, and reductive elimination. Using automatic orbital tracing in the ROET analysis, we identified the reactive orbitals for these IRCs. Consequently, we revealed the sequential electron motions driving these processes through animations, clarifying the electronic roles of the Pd center, the auxiliary ligand, and the Grignard reagent. These electron motions are consistent with experimental observations, indicating that the electron motions driving metal complex reactions can be effectively represented by changes in a single molecular orbital.

Indexed as

Cross-coupling reactionDensity functional theoryElectronic theoryGrignard reagentMetal complex reactionOrbital energy

Identifiers

PMID39910163

DOI10.1038/s41598-025-88207-w

PMCPMC11799442

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